Asymmetric Synthesis of Chiral 1,3-Dimethyl Units Through a Double Michael Reaction of Nitromethane and Crotonaldehyde Catalyzed by Diphenylprolinol Silyl Ether

Yujiro Hayashi; Shunsuke Toda

doi:10.1055/s-0037-1611644

Synlett, Table of Contents

CC BY ND NC 4.0 · Synlett 2019; 30(04): 442-448
DOI: 10.1055/s-0037-1611644

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Asymmetric Synthesis of Chiral 1,3-Dimethyl Units Through a Double Michael Reaction of Nitromethane and Crotonaldehyde Catalyzed by Diphenylprolinol Silyl Ether

Yujiro Hayashi *

Department of Chemistry, Graduate School of Science, Tohoku University, 6-3 Aramaki-Aza Aoba, Aoba-ku, Sendai 980-8578, Japan Email: yhayashi@m.tohoku.ac.jp

,

Shunsuke Toda

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Abstract

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Published as part of the 30 Years SYNLETT – Pearl Anniversary Issue

Abstract

An efficient synthetic route to install chiral 1,3-dimethyl units through a double Michael reaction of crotonaldehyde and nitromethane catalyzed by diphenylprolinol silyl ether is developed. Either 1,3-syn- or 1,3-anti-dimethyl units are obtained selectively depending on the enantiomer of the diphenylprolinol silyl ether catalyst used. The side chain of pneumocandin B₀ is synthesized enantioselectively by using the present method as a key step.

Key words

organocatalyst - Michael reaction - asymmetric synthesis - diastereoselective reaction - diphenylprolinol silyl ether

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References

References and Notes
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