Highly stereodivergent generation of the Z- and E-enolates of a β-amino ester via conjugate addition to methyl crotonate by using lithium N-benzyltrimethylsilylamide as a nitrogen nucleophile, and application to stereoselective aldol reactions

Tadao Uyehara; Naoki Asao; Yoshinori Yamamoto

doi:10.1039/C39890000753

Highly stereodivergent generation of the Z- and E-enolates of a β-amino ester via conjugate addition to methyl crotonate by using lithium N-benzyltrimethylsilylamide as a nitrogen nucleophile, and application to stereoselective aldol reactions

Tadao Uyehara, Naoki Asao, Yoshinori Yamamoto

Research output: Contribution to journal › Article › peer-review

31 Citations (Scopus)

Abstract

Methods for highly stereoselective generation of both Z- and E-enolates of a β-amino ester have been developed on the basis of a conjugate addition of lithium N-benzyltrimethylsilylamide to methyl crotonate and applied to stereoselective synthesis of anti,syn- and syn,anti-β-amino-β′- hydroxy esters by treatment with aldehyde.

Original language	English
Pages (from-to)	753-754
Number of pages	2
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	12
DOIs	https://doi.org/10.1039/C39890000753
Publication status	Published - 1989 Jan 1

ASJC Scopus subject areas

Molecular Medicine

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Uyehara, T., Asao, N., & Yamamoto, Y. (1989). Highly stereodivergent generation of the Z- and E-enolates of a β-amino ester via conjugate addition to methyl crotonate by using lithium N-benzyltrimethylsilylamide as a nitrogen nucleophile, and application to stereoselective aldol reactions. Journal of the Chemical Society, Chemical Communications, (12), 753-754. https://doi.org/10.1039/C39890000753

Highly stereodivergent generation of the Z- and E-enolates of a β-amino ester via conjugate addition to methyl crotonate by using lithium N-benzyltrimethylsilylamide as a nitrogen nucleophile, and application to stereoselective aldol reactions. / Uyehara, Tadao; Asao, Naoki; Yamamoto, Yoshinori.

In: Journal of the Chemical Society, Chemical Communications, No. 12, 01.01.1989, p. 753-754.

Research output: Contribution to journal › Article › peer-review

Uyehara, T, Asao, N & Yamamoto, Y 1989, 'Highly stereodivergent generation of the Z- and E-enolates of a β-amino ester via conjugate addition to methyl crotonate by using lithium N-benzyltrimethylsilylamide as a nitrogen nucleophile, and application to stereoselective aldol reactions', Journal of the Chemical Society, Chemical Communications, no. 12, pp. 753-754. https://doi.org/10.1039/C39890000753

Uyehara T, Asao N, Yamamoto Y. Highly stereodivergent generation of the Z- and E-enolates of a β-amino ester via conjugate addition to methyl crotonate by using lithium N-benzyltrimethylsilylamide as a nitrogen nucleophile, and application to stereoselective aldol reactions. Journal of the Chemical Society, Chemical Communications. 1989 Jan 1;(12):753-754. https://doi.org/10.1039/C39890000753

Uyehara, Tadao ; Asao, Naoki ; Yamamoto, Yoshinori. / Highly stereodivergent generation of the Z- and E-enolates of a β-amino ester via conjugate addition to methyl crotonate by using lithium N-benzyltrimethylsilylamide as a nitrogen nucleophile, and application to stereoselective aldol reactions. In: Journal of the Chemical Society, Chemical Communications. 1989 ; No. 12. pp. 753-754.

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