An unexpected highly stereoselective double aza-Baylis - Hillman reaction of sulfonated imines with phenyl vinyl ketone

Journal of Organic Chemistry

Volumn 68, Issue 12, 2003, Pages 4784-4790

  Shi, Min ^a   Xu, Yong Mei ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

LEWIS BASE;

ALKALINITY; CHEMICAL REACTIONS; SULFUR COMPOUNDS;

KETONES;

1,4 DIAZABICYCLO[2.2.2]OCTANE; BASE; IMINE; KETONE DERIVATIVE; SULFONIC ACID DERIVATIVE;

ARTICLE; AZA BAYLIS HILLMAN REACTION; CHEMICAL REACTION; REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY;

EID: 0038278402     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034114f     Document Type: Article

References (39)

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30. For previous reports related to the aza-Baylis - Hillman reaction of methyl acrylate with sulfonated imines, please see: (a) Perlmutter, P.; Teo, C. C. Tetrahedron Lett. 1984, 25, 5951. (b) Takagi, M.; Yamamoto, K. Tetrahedron 1991, 47, 8869. For previous reports related to the aza-Baylis - Hillman reaction of MVK with imine generated in situ, please see: (c) Bertenshow, S.; Kahn, M. Tetrahedron Lett. 1989, 30, 2731. (d) Balan, D.; Adolfsson, H. J. Org. Chem. 2002, 67, 2329 and references therein. The aza-Baylis - Hillman reaction of sulfonated imines with PVK has not been examined before.
31. For previous reports related to the aza-Baylis - Hillman reaction of methyl acrylate with sulfonated imines, please see: (a) Perlmutter, P.; Teo, C. C. Tetrahedron Lett. 1984, 25, 5951. (b) Takagi, M.; Yamamoto, K. Tetrahedron 1991, 47, 8869. For previous reports related to the aza-Baylis - Hillman reaction of MVK with imine generated in situ, please see: (c) Bertenshow, S.; Kahn, M. Tetrahedron Lett. 1989, 30, 2731. (d) Balan, D.; Adolfsson, H. J. Org. Chem. 2002, 67, 2329 and references therein. The aza-Baylis - Hillman reaction of sulfonated imines with PVK has not been examined before.
32. For previous reports related to the aza-Baylis - Hillman reaction of methyl acrylate with sulfonated imines, please see: (a) Perlmutter, P.; Teo, C. C. Tetrahedron Lett. 1984, 25, 5951. (b) Takagi, M.; Yamamoto, K. Tetrahedron 1991, 47, 8869. For previous reports related to the aza-Baylis - Hillman reaction of MVK with imine generated in situ, please see: (c) Bertenshow, S.; Kahn, M. Tetrahedron Lett. 1989, 30, 2731. (d) Balan, D.; Adolfsson, H. J. Org. Chem. 2002, 67, 2329 and references therein. The aza-Baylis - Hillman reaction of sulfonated imines with PVK has not been examined before.
33. w = 0.0930.
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