Mannich-Type Reactions of Aldimines and Hetero Diels-Alder Reactions of Aldehydes Catalyzed by Anion-Type Lewis Bases Derived from a Single Molecule — Oak Academic Publishing
Research ArticleOpen AccessGoogle Scholar indexed
Mannich-Type Reactions of Aldimines and Hetero Diels-Alder Reactions of Aldehydes Catalyzed by Anion-Type Lewis Bases Derived from a Single Molecule
Department of Chemistry, National Defense Academy, Hashirimizu, Yokosuka, Japan
,
Department of Chemistry, National Defense Academy, Hashirimizu, Yokosuka, Japan
,
Department of Chemistry, National Defense Academy, Hashirimizu, Yokosuka, Japan
,
Department of Chemistry, National Defense Academy, Hashirimizu, Yokosuka, Japan
1 Department of Chemistry, National Defense Academy, Hashirimizu, Yokosuka, Japan
2 Department of Chemistry, National Defense Academy, Hashirimizu, Yokosuka, Japan
3 Department of Chemistry, National Defense Academy, Hashirimizu, Yokosuka, Japan
4 Department of Chemistry, National Defense Academy, Hashirimizu, Yokosuka, Japan
Mannich-type reactions of aldimines with silyl enolates and hetero Diels-Alder reactions of aldehydes with Danishef-sky’s diene in the presence of anion catalysts derived from proline were performed to afford the corresponding products in high yields.
G. Guillena, C. Nájera and D. J. Ramón, “Enantioselective Direct Aldol Reaction: The Blossoming of Modern Organocatalysis,” Tetrahedron: Asymmetry, Vol. 18, No. 19, 2007, pp. 2249-2293. doi:10.1016/j.tetasy.2007.09.025
A.Ting and S. E. Schaus, “Organocatalytic Asymmetric Mannich Reactions: New Methodology, Catalyst Design, and Synthetic Applications,” European Journal of Organic Chemistry, Vol. 2007, No. 35, 2007, pp. 5797-5815. doi:10.1002/ejoc.200700409
H. Kotsuki, H. Ikishima and A. Okuyama, “Organocatalytic Asymmetric Synthesis Using Proline and Related Molecules. Part 1,” Heterocycles, Vol. 75, No. 3, 2008, pp. 493-529. doi:10.3987/REV-07-620
H. Kotsuki, H. Ikishima and A. Okuyama, “Organocatalytic Asymmetric Synthesis Using Proline and Related Molecules. Part 2,” Heterocycles, Vol. 75, No. 4, 2008, pp. 757-797. doi:10.3987/REV-07-621
P. Melchiorre, M. Marigo, A. Carlone and G. Bartoli, “Asymmetric Aminocatalysis—Gold Rush in Organic Chemistry,” Angewandte Chemie International Edition, Vol. 47, No. 33, 2008, pp. 6138-6171. doi:10.1002/anie.200705523
M. Gruttadauria, F. Giacalone and R. Noto, “Supported proline and proline-derivatives as recyclable organocatalysts,” Chemical Society Reviews, Vol. 37, No. 8, 2008, pp. 1666-1688. doi:10.1039/b800704g
A.-N. Alba, X. Companyó, M. Viciao and R. Rios, “Organocatalytic Domino Reactions,” Current Organic Chemistry, Vol. 13, No. 14, 2009, pp. 1432-1474. doi:10.2174/138527209789055054
?. Toma, M. Me?iarová, R. ?ebesta, “Are Ionic Liquids Suitable Media for Organocatalytic Reactions?” European Journal of Organic Chemistry, Vol. 2009, No. 3, 2009, pp. 321-327. doi:10.1002/ejoc.200800809
H. Pellissier, “Asymmetric Organocatalytic Cycloaddi- tions,” Tetrahedron, Vol. 68, No. 10, 2012, pp. 2197- 2232. doi:10.1016/j.tet.2011.10.103
B. Simmons, A. M. Walji and D. W. C. MacMillian, “Cycle-Specific Organocascade Catalysis: Application to Olefin Hydroamination, Hydro-oxidation, and Amino- oxidation, and to Natural Product Synthesis,” Ange- wandte Chemie International Edition, Vol. 48, No. 24, 2009, pp. 4349-4353. doi:10.1002/anie.200900220
C. Chandler, P. Galzerano, A. Michrowska and B. List, “The Proline-Catalyzed Double Mannich Reaction of Acetaldehyde with N-Boc Imines,” Angewandte Chemie International Edition, Vol. 48, No. 11, 2009, pp. 1978- 1980. doi:10.1002/anie.2008060s49
S. Chercheja, T. Rothenbücher and P. Eilbracht, “Tandem Metal and Organocatalysis in Sequential Hydroformyla- tion and Enantioselective Mannich Reactions,” A Advanced Synthesis & Catalysis, Vol. 351, No. 3, 2009, pp. 339-344. doi:10.1002/adsc.200800720
A. Odedra and P. H. Seeberger, “5-(Pyrrolidin-2-yl)- tetrazole-Catalyzed Aldol and Mannich Reactions: Acceleration and Lower Catalyst Loading in a Continuous- Flow Reactor,” Angewandte Chemie International Edition, Vol. 48, No. 15, 2009, pp. 2699-2702. doi:10.1002/anie.200804407
X. Ding, H.-L. Jiang, C.-J. Zhu and Y.-X. Cheng, “Direct Asymmetric α-Amination of Aldehydes with azodicarboxylates in Ionic Liquids Catalyzed by Imidazolium Ion- Tagged Proline Organocatalyst,” Tetrahedron Letters, Vol. 51, No. 47, 2010, pp. 6105-6107. doi:10.1016/j.tetlet.2010.09.036
V. Rawat, P. V. Chouthaiwale, V. B. Chavan, G. Surya- vanshi and A. Sudalai, “A Facile Enantioselective Synthesis of (S)-N-(5-Chlorothiophene-2-sulfonyl)-β,β-diethyla-laninol via Proline-Catalyzed Asymmetric α-Ami- nooxylation and α-Amination of Aldehyde,” Tetrahedron Letters, Vol. 51, No. 50, 2010, pp. 6565-6567. doi:10.1016/j.tetlet.2010.10.029
F. Kelleher, S. Kelly, J. Watts and V. McKee, “Struc- ture—Reactivity Relationships of L-Proline Derived Spirolactams and α-Methyl Prolinamide Organocatalysts in the Asymmetric Michael Addition Reaction of Aldehydes to Nitroolefins,” Tetrahedron, Vol. 66, No. 19, 2010, pp. 3525-3536. doi:10.1016/j.tet.2010.03.002
W.-H. Wang, T. Abe, X.-B. Wang, K. Kodama, T. Hirose and G.-Y. Zhang, “Self-Assembled Proline-Amino Thiou-reas as Efficient Organocatalysts for the Asymmetric Michael Addition of Al-dehydes to Nitroolefins,” Tetrahedron: Asymmetry, Vol. 21, No. 24, 2010, pp. 2925- 2933. doi:10.1016/j.tetasy.2010.11.025
S. P. Panchgalle, H. B. Bidwai, S. P. Chavan and U. R. Kalkote, “Organocatalytic Asymmetric Synthesis of (?)- δ-Coniceine Based on Sequential Proline-Catalyzed Asym-metric α-Amination—HWE Olefination,” Tetrahedron: Asymmetry, Vol. 21, No. 19, 2010, pp. 2399-2401. doi:10.1016/j.tetasy.2010.08.009
A. K. Sharma and R. B. Sunoj, “Enamine versus Oxazolidinone: What Controls Stereoselectivity in Proline- Catalyzed Asymmetric Aldol Reactions?” Angewandte Chemie International Edition, Vol. 49, No. 36, 2010, pp. 6373-6377. doi:10.1002/anie.201001588
N. Gy?rffy, A. Tungler and M. Fodor, “Stereodifferentiation in Heterogeneous Catalytic Hydrogenation. Kinetic Resolution and Asymmetric Hydrogenation in the Pres- ence of (S)-Proline: Catalyst-Dependent Processes,” Journal of Catalysis, Vol. 270, No. 1, 2010, pp. 2-8. doi:10.1016/j.jcat.2009.10.018
M. Cui, H. Song, A. Feng, Z. Wang and Q. Wang, “Asymmetric Synthesis of (R)-Antofine and (R)-Cryp- topleurine via Proline-Catalyzed Sequential α-Aminoxylation and Horner-Wadsworth-Emmons Olefination of Aldehyde,” The Journal of Organic Chemistry, Vol. 75, No. 20, 2010, pp. 7018-7021. doi:10.1021/jo101510x
H. Suga, T. Arikawa, K. Itoh, Y. Okumura, A. Kakehi and M. Shiro, “Asymmetric 1,3-Dipolar Cycloaddition Reactions of Azomethine Imines with Acrolein Catalyzed by L-Proline and Its Derivatives,” Heterocycles, Vol. 81, No. 7, 2010, pp. 1669-1688. doi:10.3987/COM-10-11967
E. Ververková, J. ?trasserová, R. ?ebesta and ?. Toma, “Asymmetric Mannich Reaction Catalyzed by N-Aryl- sulfonyl-L-proline Amides,” Tetrahedron: Asymmetry, Vol. 21, No. 1, 2010, pp. 58-61. doi:10.1016/j.tetasy.2009.12.013
M. Lu, Y. Lu, P. K. A. Tan, Q. Y. Lau and G. Zhong, “Highly Enantioselective Synthe-sis of Fluorinated b-Ami- no Ketones via Asymmetric Organocatalytic Mannich Reactions: A Case Study of Unusual Reversal of Regi- oselectivity,” Synlett, 2011, pp. 477-480. doi:10.1055/s-0030-1259513
M .Penhoat, D. Barbry and C. Rolando, “Direct Asymmetric Aldol Reaction Co-Catalyzed by L-Proline and Group 12 Elements Lewis Acids in the Pres-ence of Water,” Tetrahedron Letters, Vol. 52, No. 1, 2011, pp. 159- 162. doi:10.1016/j.tetlet.2010.11.014
A. Rai, A. K. Singh, S. Singh and L. D. S. Yadav, “Chiral Amine-Triggered Triple Cascade Reactions: A New Approach to Functionalized Decahydroquinolines,” Synlett, No. 3, 2011, pp. 335-340. doi:10.1055/s-0030-1259320
J. G. Hernández and E. Juaristi, “Asymmetric Aldol Reaction Organocatalyzed by (S)-Proline-Containing Dipeptides: Improved Stereoinduction under Solvent-Free Conditions,” The Journal of Organic Chemistry, Vol. 76, No. 5, 2011, pp. 1464-1467. doi:10.1021/jo1022469
D. E. Siyutkin, A. S. Kucherenko, L. L. Frolova, A. V. Kuchin and S. G. Zlotin, “2-Hydroxy-3-[(S)-prolina- mido]pinanes as Novel Bifunctional Organocatalysts for Asymmetric Aldol Reactions in Aqueous Media,” Tetrahedron: Asymmetry, Vol. 22, No. 12, 2011, pp. 1320- 1324. doi:10.1016/j.tetasy.2011.07.013
S. Fotaras, C. G. Kokotos, E. Tsandi and G. Kokotos, “Prolinamides Bearing Thiourea Groups as Catalysts for Asymmetric Aldol Reactions,” European Journal of Organic Chemistry, Vol. 2011, No. 7, 2011, pp. 1310-1317. doi:10.1002/ejoc.201001417
J. G. Hernández, V. García-López and E. Juaristi, “Solvent-Free Asymmetric Aldol Reaction Organocatalyzed by (S)-Proline-Containing Thiodipeptides under Ball- Milling Conditions,” Tetrahedron, Vol. 68, No. 1, 2012, pp. 92-97. doi:10.1016/j.tet.2011.10.093
M. Yamaguchi, T. Shiraishi and M. Hirama, “A Catalytic Enantioselective Michael Addition of a Simple Malonate to Prochiral α,β-Unsaturated Ketoses and Aldehyde,” Angewandte Chemie International Edition, Vol. 32, No. 8, 1993, pp. 1176-1178. doi:10.1002/anie.199311761
M. Yasmaguchi, Y. Igarashi, R. S. Reddy, T. Shiraishi and M. Hirama, “Catalytic Asymmetric Michael Addition of Nitroalkane to Enone and Enal,” Tet-rahedron Letters, Vol. 35, No. 44, 1994, pp. 8233-8236. doi:10.1016/0040-4039(94)88290-8
M. Yamaguchi, T. Shiraishi and M. Hirama, “Asymmetric Michael Addition of Malonate Anions to Prochiral Acceptors Catalyzed by L-Proline Rubidium Salt,” The Journal of Organic Chemistry, Vol. 61, No. 10, 1996, pp. 3520-3530. doi:10.1021/jo960216c
M. Yamaguchi, Y. Igarashi, R. S. Reddy, T. Shiraishi and M. Hirama, “Asymmetric Michael Addition of Nitroal- kanes to Prochiral Acceptors Catalyzed by Proline Ru- bidium Salts,” Tetrahedron, Vol. 53, No. 32, 1997, pp. 11223-11236. doi:10.1016/S0040-4020(97)00379-7
H. Fujisawa and T. Mukaiyama, “A Catalytic Aldol Reaction between Ketene Silyl Acetals and Aldehydes Promoted by Lithium Amide under Non-Acidic Conditions,” Chemistry Letters, Vol. 31, No. 2, 2002, pp. 182- 183. doi:10.1246/cl.2002.182
H. Fujisawa and T. Mukaiyama, “Lithium Pyrrolidone Catalyzed Aldol Reaction between Aldehyde and Trimethylsilyl Enolate,” Chemistry Letters, Vol. 31, No. 8, 2002, pp. 858-859. doi:10.1246/cl.2002.858
T. Mukaiyama H. Fujisawa and T. Nakagawa, “Lewis Base Catalyzed Aldol Reaction of Trimethylsilyl Enolates with Aldehydes,” Helvetica Chimica Acta, Vol. 85, No. 12, 2002, pp. 4518-4531.doi:10.1002/hlca.200290025
T. Mukaiyama, T. Nakagawa and H. Fujisawa, “Lewis Base Catalyzed Michael Reaction between Ketene Silyl Acetals and α,β-Unsaturated Carbonyl Compounds,” Chemistry Letters, Vol. 32, No. 1, 2003, pp. 56-57. doi:10.1246/cl.2003.56
T. Nakagawa, H. Fujisawa and T. Mukaiyama, “Lithium Acetate-Catalyzed Aldol Reaction between Aldehyde and Trimethylsilyl Enolate,” Chemistry Letters, Vol. 32, No. 5, 2003, pp. 462-463. doi:10.1246/cl.2003.462
T. Nakagawa, H. Fujisawa and T. Mukaiyama, T. “Lithium Acetate Catalyzed Aldol Reaction between Aldehyde and Trimethylsilyl Enolate in a Dimethylformamide—H2O Solvent,” Chemistry Letters, Vol. 32, No. 8, 2003, pp. 696-697. doi:10.1246/cl.2003.696
T. Nakagawa, H. Fujisawa and T. Mukaiyama, “Self- Promoted Aldol Reaction between Aldehyde Having Lewis Base Moiety and Trimethylsilyl Enolate,” Chemis- try Letters, Vol. 33, No. 2, 2004, pp. 92-93. doi:10.1246/cl.2004.92
T. Nakagawa, H. Fujisawa, Y. Nagata and T. Mukaiyama, “Lithium Acetate-Catalyzed Michael Reaction between Trimethylsilyl Enolate and α,β-Unsaturated Carbonyl Compound,” Chemistry Letters, Vol. 33, No. 8, 2004, pp. 1016-1017. doi:10.1246/cl.2004.1016
T. Mukaiyama, T. Tozawa and H. Fujisawa, “Lithium Alkoxide-Promoted Michael Reaction between Silyl Eno- lates and α,β-Unsaturated Carbonyl Compounds,” Chemistry Letters, Vol. 33, No. 11, 2004, pp. 1410-1411. doi:10.1246/cl.2004.1410
E. Takahashi, H. Fujisawa, T. Yanai and T. Mukaiyama, “Lewis Base-Catalyzed Strecker-Type Reaction between Trimethylsilyl Cyanide and N-Tosylimines in Water- containing DMF,” Chemistry Letters, Vol. 34, No. 3, 2005, pp. 318-319. doi:10.1246/cl.2005.318
Y. Sato, H. Fujisawa and T. Mukaiyama, “Lewis Base -Catalyzed [2,3]-Wittig Rearrangement of Silyl Enolates Generated from α-Allyloxy Ketones,” Chemistry Letters, Vol. 34, No. 4, 2005, pp. 588-589. doi:10.1246/cl.2005.588
E. Takahashi, H. Fujisawa, T. Yanai and T. Mukaiyama, “Lewis Base-Catalyzed Diastereoselective Strecker-Type Reaction between Trimethylsilyl Cyanide and Chiral Sulfinimines,” Chemistry Letters, Vol. 34, No. 4, 2005, pp. 604-605. doi:10.1246/cl.2005.604
Y. Kawano, H. Fujisawa and T. Mukaiyama, “Lithium Acetate-Catalyzed Crossed Aldol Reaction between Al- dehydes and Trimethylsilyl Enolates Generated from Other Aldehydes,” Chemistry Letters, Vol. 34, No. 4, 2005, pp. 614-615. doi:10.1246/cl.2005.614
Y. Kawano, N. Kaneko and T. Mukaiyama, “Lewis Base- Catalyzed Cyanomethylation of Carbonyl Compounds with (Trimethylsilyl)Acetonitrile,” Chemistry Letters, Vol. 34, No. 11, 2005, pp. 1508-1509. doi:10.1246/cl.2005.1508
M. Hatano, T. Ikeno, T. Miya-moto and K. Ishihara, “Chiral Lithium Binaphtholate Aqua Complex as a Highly Effective Asymmetric Catalyst for Cy-anohydrin Synthesis,” Journal of the American Chemical Society, Vol. 127, No. 31, 2005, pp. 10776-10777. doi:10.1021/ja051125c
Y. Kawano, N. Kaneko and T. Mukaiyama, “Lewis Base- Catalyzed Perfluoroalkylation of Carbonyl Compounds and Imines with (Perfluoroalkyl)Trimethylsilane,” Bulletin of the Chemical Society of Japan, Vol. 79, No. 7, 2006, pp. 1133-1145. doi:10.1246/bcsj.79.1133
H. Fujisawa, E .Takahashi, T. Nagasawa and T. Mukaiyama, “Lewis Base-Catalyzed Mannich-Type Reaction between Aldimine and Trimethylsilyl Enolate,” Chemistry Letters, Vol. 32, No. 11, 2003, pp. 1036-1037. doi:10.1246/cl.2003.1036
E. Takahashi, H. Fujisawa and T. Mukaiyama, “Lithium Acetate-Catalyzed Mannich-Type Reaction between Tri-methylsilyl Enolates and Aldimines in a Water-Contain- ing DMF,” Chemistry Letters, Vol. 33, No. 7, 2004, pp. 936-937. doi:10.1246/cl.2004.936
E. Takahashi, H. Fujisawa and T. Mukaiyama, “Lewis Base-Catalyzed Anti-Selective Mannich-Type Reaction between Trimethylsilyl Enolates and Aldimines,” Chemistry Letters, Vol. 34, No. 1, 2005, pp. 84-85. doi:10.1246/cl.2005.84
E. Takahashi, H. Fujisawa, T. Yanai and T. Mukaiyama, “One-Pot Synthesis of β-Lactams from Aldimines and Ketene Silyl Acetals by Tandem Lewis Base-Catalyzed Mannich-Type Addition and Cyclization,” Chemistry Let- ters, Vol. 34, No. 2, 2005, pp. 216-217. doi:10.1246/cl.2005.216
H. Fujisawa, E. Takahashi and T. Mukaiyama, “Lewis Base Catalyzed Mannich-Type Reactions between Trime- thylsilyl Enol Ethers and Aldimines,” Chemistry—A European Journal, Vol. 12, No. 19, 2006, pp. 5082-5093. doi:10.1002/chem.200500821
T. Mukaiyama, T. Kitazawa and H. Fujisawa, “A Lewis Base-Catalyzed Hetero Diels—Alder Reaction between Aldehydes and the Danishefsky’s Diene,” Chemistry Letters, Vol. 35, No. 3, 2006, pp. 328-329. doi:10.1246/cl.2006.328
S. Hanessian and V. Pham, “Catalytic Asymmetric Conjugate Addition of Nitroalkanes to Cycloalkenones,” Organic Letters, Vol. 2, No. 19, 2000, pp. 2975-2978. doi:10.1021/ol000170g
S. Hanessian, Z. Shao and J. S. Warrier, “Optimization of the Catalytic Asymmetric Addition of Nitroalkanes to Cyclic Enones with Trans-4,5-methano-l-proline,” Organic Letters, Vol. 8, No. 21, 2006, pp. 4787-4786. doi:10.1021/ol0618407
R. G. Kostyanovsky, I. M. Gella, V. I. Markov and Z. E. Samojlova, “Asymmetrical Nonbridgehead Nitrogen—IV: Chiroptical properties of the Amines, N-Chloroamines and Cyanamides,” Tetrahedron, Vol. 30, No. 1, 1974, pp. 39-45. doi:10.1016/S0040-4020(01)97214-X
T. Rosen, S. W. Fesik, D. T. W. Chu and A. G. Pernet, “Asymmetric Synthesis of 2-Substituted (4S)-4-Amino- pyrrolidines. SN2 Displacement at the 4-Position of the Pyrrolidine Moiety,” Synthesis, No. 1, 1988, pp. 40-44. doi:10.1055/s-1988-27459
Y. N. Belokon’, I. E. Zel’tzer, V. I. Bakhmutov, M. B. Saporovskaya, M. G. Ryzhov, A. I. Yanovsky, Y. T. Struchkov and V. M. Belikov, “Asymmetric Synthesis of Threonine and Partial Res-olution and Retroracemization of .Alpha.-Amino Acids via Copper(II) Complexes of Their Schiff Bases with (S)-2-N-(N'-Benzylprolyl)amino- benzaldehyde and (S)-2-N-(N'-Benzylprolyl)amino-aceto- phenone. Crystal and Molecular Structure of a Copper(II) Complex of Glycine Schiff Base with (S)-2-N-(N'-ben- zylprolyl)aminoacetophen
J. Long, J. Hu, X. Shen, B. Ji and K. Ding, “Discovery of Exceptionally Efficient Catalysts for Solvent-Free Enan- tioselective Hetero-Diels—Alder Reaction,” Journal of the American Chemical Society, Vol. 124, No. 1, 2002, pp. 10-11. doi:10.1021/ja0172518
H. Furuno, T. Hayano, T. Kambara, Y. Sugimoto, T. Hanamoto, Y. Tanaka, Y. Z. Jin, T. Kagawa and J. Inanaga, “Chiral Rare Earth Organo-phosphates as Homogeneous Lewis Acid Catalysts for the highly enantioselective Hetero-Diels—Alder Reactions,” Tet-rahedron, Vol. 59, No. 52, 2003, pp. 10509-10523. doi:10.1016/j.tet.2003.06.011
K. Aikawa, R. Irie and T. Katsuki, “Asymmetric Hetero- Diels—Alder reaction Using Chiral Cationic Metallosalen Complexes as Catalysts,” Tetra-hedron, Vol. 57, No. 5, 2001, pp. 845-851. doi:10.1016/S0040-4020(00)01048-6