Multifunctional chiral phosphine organocatalysts in catalytic asymmetric morita-baylis-hillman and related reactions

Accounts of Chemical Research

Volumn 43, Issue 7, 2010, Pages 1005-1018

  Wei, Yin ^a   Shi, Min ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77954854439     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar900271g     Document Type: Article

References (90)

1. Shibasaki, M.; Sasai, H.; Arai, T. Asymmetric Catalysis with Heterobimetallic Compounds Angew. Chem., Int. Ed. Engl. 1997, 36, 1236-1256
2. Shibasaki, M.; Yoshikawa, N. Lanthanide Complexes in Multifunctional Asymmetric Catalysis Chem. Rev. 2002, 102, 2187-2209
3. Saito, S.; Yamamoto, H. Design of Acid-Base Catalysis for the Asymmetric Direct Aldol Reaction Acc. Chem. Res. 2004, 37, 570-579
4. Tian, S.-K.; Chen, Y.; Hang, J.; Tang, L.; Mcdaid, P.; Deng, L. Asymmetric Organic Catalysis with Modified Cinchona Alkaloids Acc. Chem. Res. 2004, 37, 621-631
5. Marcelli, T.; van Maarseveen, J. H.; Hiemstra, H. Cupreines and Cupreidines: An Emerging Class of Bifunctional Cinchona Organocatalysts Angew. Chem., Int. Ed. 2006, 45, 7496-7504
6. For reviews of multifunctional catalysis, see: Sawamura, M.; Ito, Y. Catalytic Asymmetric Synthesis by Means of Secondary Interaction between Chiral Ligands and Substrates Chem. Rev. 1992, 92, 857-871
7. Steinhagen, H.; Helmchen, G. Asymmetric Two-Center Catalysis-Learning from Nature Angew. Chem., Int. Ed. Engl. 1996, 35, 2339-2342
8. van den Beuken, E. K.; Feringa, B. L. Bimetallic Catalysis by Late Transtition Metal Complexes Tetrahedron 1998, 54, 12985-13011
9. Rowlands, G. J. Ambifunctional Cooperative Catalysts Tetrahedron 2001, 57, 1865-1882
10. For reviews, see: Shibasaki, M.; Sasai, H.; Arai, T.; Iida, T. Heterobimetallic Asymmetric Catalysts. Developments and Applications Pure Appl. Chem. 1998, 70, 1027-1034
11. Shibasaki, M.; Iida, T.; Yamada, Y. M. A. Development of Multifunctional Asymmetric Catalysts and Their Application to Practical Organic Synthesis J. Synth. Org. Chem. Jpn. 1998, 56, 344-356
12. Shibasaki, M. Multifunctional Asymmetric Catalysis Chemtracts: Org. Chem. 1999, 12, 979-998
13. Shibasaki, M. Multifunctional Asymmetric Catalysis Enantiomer 1999, 4, 513-527
14. For selected reviews concerning organocatalysis, see: Dalko, P. I.; Moisan, L. Enantioselective Organocatalysis Angew. Chem., Int. Ed. 2001, 40, 3726-3748
15. Benaglia, M.; Puglisi, A.; Cozzi, F. Polymer-Supported Organic Catalysts Chem. Rev. 2003, 103, 3401-3430
16. Berkessel, A.; Gröger, H. Metal-Free Organic Catalysis in Asymmetric Synthesis. Wiley-VCH, Weinheim, Germany, 2004.
17. Special Issue: Asymmetric Organocatalysis. Acc. Chem. Res. 2004, 37, 487 - 631.
18. For reviews, see: List, B. Asymmetric Aminocatalysis Synlett 2001, 1675-1686
19. List, B. Proline-Catalyzed Asymmetric Reactions Tetrahedron 2002, 58, 5573-5590
20. List, B. Enamine Catalysis Is a Powerful Strategy for the Catalytic Generation and Use of Carbanion Equivalents Acc. Chem. Res. 2004, 37, 548-557
21. Movassaghi, M.; Jacobsen, E. N. The Simplest "Enzyme" Science 2002, 298, 1904-1905
22. Baylis, A. B.; Hillman, M. E. D. Ger. Offen 2,155,113, 1972
23. Chem. Abstr. 1972, 77, 34174q
24. Hillman, M. E. D.; Baylis, A. B. U. S. Patent 3,743,669, 1973.
25. Morita, K.; Suzuki, Z.; Hirose, H. A Tertiary Phosphine-Catalyzed Reaction of Acrylic Compounds with Aldehydes Bull. Chem. Soc. Jpn. 1968, 41, 2815-2815 For recent reviews on MBH reaction
26. Recent Advances in the Baylis-Hillman Reaction and Applications Chem. Rev. 2003, 103, 811-892
27. Basavaiah, D.; Rao, K. V.; Reddy, R. J. The Baylis-Hillman Reaction: A Novel Source of Attraction, Opportunities, and Challenges in Synthetic Chemistry Chem. Soc. Rev. 2007, 36, 1581-1588
28. Singh, V.; Batra, S. Advances in the Baylis-Hillman Reaction-Assisted Synthesis of Cyclic Frameworks Tetrahedron 2008, 64, 4511-4574
29. For reviews on aza -MBH reaction, see: Shi, Y.-L.; Shi, M. Aza-Baylis-Hillman Reactions and Their Synthetic Applications Eur. J. Org. Chem. 2007, 2150-2155
30. Declerck, V.; Martinez, J.; Lamaty, F. Aza-Baylis-Hillman reaction Chem. Rev. 2009, 109, 1-46 For reviews on enantioselective MBH reaction
31. Langer, P. New Strategies for the Development of an Asymmetric Version of the Baylis-Hillman Reaction Angew. Chem., Int. Ed. 2000, 39, 3049-3052
32. Masson, G.; Housseman, C.; Zhu, J. The Enantioselective Morita-Baylis-Hillman Reaction and Its Aza Counterpart Angew. Chem., Int. Ed. 2007, 46, 4614-4628
33. Ma, G.-N.; Jiang, J.-J.; Shi, M.; Wei, Y. Recent Extensions of the Morita-Baylis-Hillman Reaction Chem. Commun. 2009, 5496-5514 and references therein
34. For some representative reports on the asymmetric MBH/aza-MBH reaction, see: Brzezinski, L. J.; Rafel, S.; Leahy, J. W. The Asymmetric Baylis-Hillman Reaction J. Am. Chem. Soc. 1997, 119, 4317-4318
35. Aggarwal, V. K.; Castro, A. M. M.; Mereu, A.; Adams, H. The Use of Enantiomerically Pure N -sulfinimines in Asymmetric Baylis-Hillman Reactions Tetrahedron Lett. 2002, 43, 1577-1580
36. Shi, M.; Xu, Y.-M. Diastereoselective Baylis-Hillman Type Reactions of Chiral Non-Racemic N -Sulfinimines with Cyclopent-2-en-1-one Tetrahedron: Asymmetry 2002, 13, 1195-1200
37. 2AlCl and Its Application to the Stereoselective Synthesis of Unusual ?-Branched Baylis?Hillman Adducts J. Org. Chem. 1999, 64, 1061-1064
38. Krishna, P. R.; Sachwani, R.; Reddy, P. S. Asymmetric Baylis-Hillman Reaction: An Enchanting Expedition Synlett 2008, 2897-2912
39. Barrett, A. G. M.; Cook, A. S.; Kamimura, A. Asymmetric Baylis-Hillman Reactions: Catalysis Using a Chiral Pyrrolizidine Base Chem. Commun. 1998, 2533-2534
40. Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. Chiral Amine-Catalyzed Asymmetric Baylis?Hillman Reaction: A Reliable Route to Highly Enantiomerically Enriched (?-Methylene-?-hydroxy)esters J. Am. Chem. Soc. 1999, 121, 10219-10220
41. Imbriglio, J. E.; Vasbinder, M. M.; Miller, S. J. Dual Catalyst Control in the Amino Acid-Peptide-Catalyzed Enantioselective Baylis?Hillman Reaction Org. Lett. 2003, 5, 3741-3743
42. For recent mechanistic studies on MBH reaction: Santos, L. S.; Pavam, C. H.; Almeida, W. P.; Coelho, F.; Eberlin, M. N. Probing the Mechanism of the Baylis-Hillman Reaction by Electrospray Ionization Mass and Tandem Mass Spectrometry Angew. Chem., Int. Ed. 2004, 43, 4330-4333
43. Price, K. E.; Broadwater, S. J.; Jung, H. M.; McQuade, D. T. Baylis-Hillman Mechanism: A New Interpretation in Aprotic Solvents Org. Lett. 2005, 7, 147-150
44. Aggarwal, V. K.; Fulford, S. Y.; Lloyd-Jones, G. C. Reevaluation of the Mechanism of the Baylis-Hillman Reaction: Implications for Asymmetric Catalysis Angew. Chem., Int. Ed. 2005, 44, 1706-1708
45. Robiette, R.; Aggarwal, V. K.; Harvey, J. N. Mechanism of the Morita?Baylis?Hillman Reaction: A Computational Investigation J. Am. Chem. Soc. 2007, 129, 15513-15525
46. Matsui, K.; Takizawa, S.; Sasai, H. Bifunctional Organocatalysts for Enantioselective Aza-Morita?Baylis?Hillman Reaction J. Am. Chem. Soc. 2005, 127, 3680-3681
47. Matsui, K.; Tanaka, K.; Horii, A.; Takizawa, S.; Sasai, H. Conformational Lock in a Brønsted Acid-Lewis Base Organocatalyst for the aza-Morita-Baylis-Hillman Reaction Tetrahedron: Asymmetry 2006, 17, 578-583
48. For reviews of phosphine catalysis, see: Glueck, D. S. Catalytic Asymmetric Synthesis of Chiral Phosphanes Chem. - Eur. J. 2008, 14, 7108-7117
49. Methot, J. L.; Roush, W. R. Nucleophilic Phosphine Organocatalysis Adv. Synth. Catal. 2004, 346, 1035-1050
50. Lu, X.; Zhang, C.; Xu, Z. Reactions of Electron-Deficient Alkynes and Allenes under Phosphine Catalysis Acc. Chem. Res. 2001, 34, 535-544
51. Uozumi, Y.; Tanahashi, A.; Lee, S.-Y.; Hayashi, T. Synthesis of Optically Active 2-(Diary1phosphino)-1,l?-binaphthyls, Efficient Chiral Monodentate Phosphine Ligands J. Org. Chem. 1993, 58, 1945-1948
52. Shi, M.; Chen, L.-H. Chiral Phosphine Lewis Base Catalyzed Asymmetric Aza-Baylis-Hillman Reaction of N -sulfonated Imines with Methyl Vinyl Ketone and Phenyl Acrylate Chem. Commun. 2003, 1310-1311
53. Shi, M.; Xu, Y.-M. Catalytic, Asymmetric Baylis-Hillman Reaction of Imines with Methyl Vinyl Ketone and Methyl Acrylate Angew. Chem., Int. Ed. 2002, 41, 4507-4510
54. Shi, M.; Chen, L.-H.; Li, C.-Q. Chiral Phosphine Lewis Bases Catalyzed Asymmetric Aza-Baylis?Hillman Reaction of N-Sulfonated Imines with Activated Olefins J. Am. Chem. Soc. 2005, 127, 3790-3800
55. Buskens, P.; Klankermayer, J.; Leitner, W. Bifunctional Activation and Racemization in the Catalytic Asymmetric Aza-Baylis?Hillman Reaction J. Am. Chem. Soc. 2005, 127, 16762-16763
56. Shi, M.; Ma, G.-N.; Gao, J. Chiral Bifunctional Organocatalysts in Asymmetric Aza-Morita?Baylis?Hillman Reactions of Ethyl(arylimino)acetates with Methyl Vinyl Ketone and Ethyl Vinyl Ketone J. Org. Chem. 2007, 72, 9779-9781
57. Shi, M.; Zhao, G.-L. Aza-Baylis-Hillman Reactions of N -(Arylmethylene)diphenylphosphinamides with Activated Olefins in the Presence of Various Lewis Bases Adv. Synth. Catal. 2004, 346, 1205-1219
58. For (thio)urea derivatives catalyzed reactions, see: Taylor, M. S.; Jacobsen, E. N. Asymmetric Catalysis by Chiral Hydrogen-bond Donors Angew. Chem., Int. Ed. 2006, 45, 1520-1543
59. Connon, S. J. Organocatalysis Mediated by (Thio)Urea Derivatives Chem. - Eur. J. 2006, 12, 5418-5427
60. Berkessel, A.; Roland, K.; Neudörfl, J. M. Asymmetric Morita?Baylis?Hillman Reaction Catalyzed by Isophoronediamine-derived Bis(thio)urea Organocatalysts Org. Lett. 2006, 8, 4195-4198
61. Shi, Y.-L.; Shi, M. Chiral Thiourea-Phosphine Organocatalysts in the Asymmetric Aza-Morita-Baylis-Hillman Reaction Adv. Synth. Catal. 2007, 349, 2129-2135
62. Qi, M.-J.; Ai, T.; Shi, M.; Li, G. Asymmetric Catalytic Aza-Morita-Baylis-Hillman Reaction Using Chiral Bifunctional Phosphine Amides as Catalysts Tetrahedron 2008, 64, 1181-1186
63. Guan, X.-Y.; Jiang, Y.-Q.; Shi, M. Chiral Sterically Congested Phosphane-Amide Bifunctional Organocatalysts in Asymmetric Aza-Morita-Baylis- Hillman Reactions of N -sulfonated Imines with Methyl and Ethyl Vinyl Ketones Eur. J. Org. Chem. 2008, 2150-2155
64. Shi, M.; Li, C.-Q. Catalytic, Asymmetric Aza-Baylis-Hillman Reaction of N -Sulfonated Imines with 2-Cyclohexen-1-one and 2-cyclopenten-1-one in the Presence of a Chiral Phosphine Lewis Base Tetrahedron: Asymmetry 2005, 16, 1385-1391
65. Lei, Z.-Y.; Ma, G.-N.; Shi, M. A Fast Catalytic Asymmetric Aza-Morita-Baylis-Hillman Reaction of N -Sulfonated Imines with Methyl Vinyl Ketone in the Presence of Chiral Bifunctional Phosphane Lewis Bases Eur. J. Org. Chem. 2008, 3817-3820
66. Han, J.-W.; Hayashi, T. Preparation of a New MOP Ligand Containing a Long-Chain Alkyl Group and Its Use for Palladium-Catalyzed Asymmetric Hydrosilylation of Cyclic 1,3-Dienes Chem. Lett. 2001, 976-977
67. Shi, M.; Chen, L.-H.; Teng, W.-D. Asymmetric Aza-Morita-Baylis-Hillman Reaction of N -Sulfonated Imines with Methyl Vinyl Ketone Catalyzed by Chiral Phosphine Lewis Bases Bearing Perfluoroalkanes as "Pony Tails" Adv. Synth. Catal. 2005, 347, 1781-1789
68. Liu, Y.-H.; Chen, L.-H.; Shi, M. Asymmetric Aza-Morita-Baylis-Hillman Reaction of N -Sulfonated Imines with Activated Olefins Catalyzed by Chiral Phosphine Lewis Bases Bearing Multiple Phenol Groups Adv. Synth. Catal. 2006, 348, 973-979
69. Matsui, K.; Takizawa, S.; Sasai, H. A Brønsted Acid and Lewis Base Organocatalyst for the Aza-Morita-Baylis-Hillman Reaction Synlett 2006, 761-765
70. Ito, K.; Nishida, K.; Gotauda, T. Highly Enantioselective Aza-Morita-Baylis-Hillman Reaction with a Bisphenol-based Bifunctional Organocatalyst Tetrahedron Lett. 2007, 48, 6147-6149
71. For dendrimeric phosphines in asymmetric catalysis, see: Caminade, A.-M.; Servin, P.; Laurent, R.; Majoral, J.-P. Dendrimeric Phosphines in Asymmetric Catalysis Chem. Soc. Rev. 2008, 37, 56-67
72. Liu, Y.-H.; Shi, M. Dendritic Chiral Phosphine Lewis Bases-Catalyzed Asymmetric Aza-Morita-Baylis-Hillman Reaction of N -Sulfonated Imines with Activated Olefins Adv. Synth. Catal. 2008, 350, 122-128
73. Garnier, J.-M.; Anstiss, C.; Liu, F. Enantioselective Trifunctional Organocatalysts for Rate-Enhanced Aza-Morita-Baylis-Hillman Reactions at Room Temperature Adv. Synth. Catal. 2009, 351, 331-338
74. Garnier, J.-M.; Liu, F. Trifunctional Organocatalyst-Promoted Counterion Catalysis for Fast and Enantioselective Aza-Morita-Baylis-Hillman Reactions at Ambient Temperature Org. Biomol. Chem. 2009, 7, 1272-1275
75. Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. Synthesis of Chiral Hydroxyl Phospholane from D-manitol and Their Use in Asymmetric Catalytic Reactions J. Org. Chem. 2000, 65, 3489-3496
76. Shi, M.; Liu, Y.-H.; Chen, L.-H. Asymmetric Catalysis of Morita-Baylis-Hillman Reactions by Chiral Phosphine Lewis Bases Bearing Multiple Phenol Groups Chirality 2007, 19, 124-128
77. Lei, Z.-Y.; Liu, X.-G.; Shi, M.; Zhao, M. Binfunctional Chiral Phosphine-Containing Lewis Base Catalyzed Asymmetric Morita-Baylis-Hillman Reaction of Aldehydes with Activated Alkenes Tetrahedron: Asymmetry 2008, 19, 2058-2062
78. Yuan, K.; Zhang, L.; Song, H.-L.; Hu, Y.; Wu, X.-Y. Chiral Phosphinothiourea Organocatalyst in the Enantioselective Morita-Baylis-Hillman Reactions of Aromatic Aldehydes with Methyl Vinyl Ketone Tetrahedron Lett. 2008, 49, 6262-6264
79. For other [3 + 2] cycloaddition reactions, see: Wilson, J. E.; Fu, G. C. Synthesis of Functionalized Cyclopentenes through Catalytic Asymmetric [3 + 2] Cycloadditions of Allenes with Enones Angew. Chem., Int. Ed. 2006, 45, 1426-1429
80. Jean, L.; Marinetti, A. Phosphine-Catalyzed Enantioselective [3 + 2] Annulations of 2,3-Butadienoates with Imines Tetrahedron Lett. 2006, 47, 2141-2145
81. Lu, Z.; Zheng, S.; Lu, X. An Unexpected Phosphine-Catalyzed [3 + 2] Annulation. Synthesis of Highly Functionalized Cyclopentenes Org. Lett. 2008, 10, 3267-3270 For some similar works on the phosphine-catalyzed [4 + 2] annulation between imines and allenoates
82. Zhu, X.-F.; Lan, J.; Kwon, O. An Expedient Phosphine-Catalyzed [4 + 2] Annulation: Synthesis of Highly Functionalized Tetrahydropyridines J. Am. Chem. Soc. 2003, 125, 4716-4717
83. For mechanistic study on [3 + 2] cycloaddition reactions, see: Xia, Y.; Liang, Y.; Chen, Y.; Wang, M.; Jiao, L.; Huang, F.; Liu, S.; Li, Y.; Yu, Z.-X. An Unexpected Role of a Trace Amount of Water in Catalyzing Proton Transfer in Phosphine-Catalyzed (3 + 2) Cycloaddition of Allenoates and Alkenes J. Am. Chem. Soc. 2007, 129, 3470-3471
84. Cowen, B. J.; Miller, S. J. Enantioselective [3 + 2]-Cycloadditions Catalyzed by a Protected, Multifunctional Phosphine-Containing ?-Amino Acid J. Am. Chem. Soc. 2007, 129, 10988-10989
85. Fang, Y.-Q.; Jacobsen, E. N. Cooperative, Highly Enantioselective Phosphinothiourea Catalysis of Imine?Allene [3 + 2] Cycloadditions J. Am. Chem. Soc. 2008, 130, 5660-5661
86. Jiang, Y.-Q.; Shi, Y.-L.; Shi, M. Chiral Phosphine-Catalyzed Enantioselective Construction of ?-Butenolides through Substitution of Morita?Baylis?Hillman Acetates with 2-Trimethylsilyloxy Furan J. Am. Chem. Soc. 2008, 130, 7202-7203
87. Cho, C.-W.; Kong, J.-R.; Krische, M. J. Phosphine-Catalyzed Regiospecific Allylic Amination and Dynamic Kinetic Resolution of Morita?Baylis?Hillman Acetates Org. Lett. 2004, 6, 1337-1339
88. Cho, C.-W.; Krische, M. J. Regio- and Stereoselective Construction of ?-Butenolides through Phosphine-Catalyzed Substitution of Morita-Baylis-Hillman Acetates: An Organocatalytic Allylic Alkylation Angew. Chem., Int. Ed. 2004, 43, 6689-6691
89. Zhang, T.-Z.; Dai, L.-X.; Hou, X.-L. Enantioselective Allylic Substitution of Morita-Baylis-Hillman Adducts Catalyzed by Planar Chiral [2.2]paracyclophane Monophosphines Tetrahedron: Asymmetry 2007, 18, 1990-1994
90. Ma, G.-N.; Cao, S.-H.; Shi, M. Chiral Phosphine-Catalyzed Regio- and Enantioselective Allylic Amination of Morita-Baylis-Hillman Acetates Tetrahedron: Asymmetry 2009, 20, 1086-1092