Synthesis of enantiomerically enriched Baylis-Hillman alcohols from their acetates: Combination of kinetic resolution during the salt formation with (DHQD)2PHAL and following asymmetric induction during hydrolysis with NaHCO3 as a water surrogate

Tetrahedron Letters

Volumn 43, Issue 50, 2002, Pages 9141-9146

  Kim, Jae Nyoung ^a   Lee, Hong Jung ^a   Gong, Ji Hyeon ^a  

^a Chonnam National University   (South Korea)

Author keywords

Asymmetric induction; Baylis Hillman alcohol; Cinchona alkaloid; Kinetic resolution; Water surrogate

Indexed keywords

ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; BICARBONATE; CINCHONIDINE; WATER;

ACETYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; BAYLIS HILLMAN REACTION; CHEMICAL REACTION; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; HYDROLYSIS; KINETICS; RACEMIC MIXTURE;

CINCHONA;

EID: 0037049208     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02274-8     Document Type: Article

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27. For the enantioselective acylation with kinetic resolution strategy, see: (a) Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809; (b) Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1997, 119, 2584; (c) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638; (d) Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430; (e) Taylor, S. J.; Morken, J. P. Science 1998, 280, 267; (f) Ruble, J. C.; Fu, G. C. J. Org. Chem. 1996, 61, 7230; (g) Copeland, G. T.; Jarvo, E. R.; Miller, S. J. J. Org. Chem. 1998, 63, 6784; (h) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169; (i) Spivey, A. C.; Fekner, T.; Spey, S. E.; Adams, H. J. Org. Chem. 1999, 64, 9430.
28. For the enantioselective acylation with kinetic resolution strategy, see: (a) Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809; (b) Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1997, 119, 2584; (c) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638; (d) Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430; (e) Taylor, S. J.; Morken, J. P. Science 1998, 280, 267; (f) Ruble, J. C.; Fu, G. C. J. Org. Chem. 1996, 61, 7230; (g) Copeland, G. T.; Jarvo, E. R.; Miller, S. J. J. Org. Chem. 1998, 63, 6784; (h) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169; (i) Spivey, A. C.; Fekner, T.; Spey, S. E.; Adams, H. J. Org. Chem. 1999, 64, 9430.
29. For the enantioselective acylation with kinetic resolution strategy, see: (a) Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809; (b) Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1997, 119, 2584; (c) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638; (d) Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430; (e) Taylor, S. J.; Morken, J. P. Science 1998, 280, 267; (f) Ruble, J. C.; Fu, G. C. J. Org. Chem. 1996, 61, 7230; (g) Copeland, G. T.; Jarvo, E. R.; Miller, S. J. J. Org. Chem. 1998, 63, 6784; (h) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169; (i) Spivey, A. C.; Fekner, T.; Spey, S. E.; Adams, H. J. Org. Chem. 1999, 64, 9430.
30. For the enantioselective acylation with kinetic resolution strategy, see: (a) Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809; (b) Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1997, 119, 2584; (c) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638; (d) Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430; (e) Taylor, S. J.; Morken, J. P. Science 1998, 280, 267; (f) Ruble, J. C.; Fu, G. C. J. Org. Chem. 1996, 61, 7230; (g) Copeland, G. T.; Jarvo, E. R.; Miller, S. J. J. Org. Chem. 1998, 63, 6784; (h) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169; (i) Spivey, A. C.; Fekner, T.; Spey, S. E.; Adams, H. J. Org. Chem. 1999, 64, 9430.
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