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

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

SCI - Chemistry

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

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 B ₀ is synthesized enantioselectively by using the present method as a key step.

Original language	English
Pages (from-to)	442-448
Number of pages	7
Journal	Synlett
Volume	30
Issue number	4
DOIs	https://doi.org/10.1055/s-0037-1611644
Publication status	Published - 2019

Keywords

Michael reaction
asymmetric synthesis
diastereoselective reaction
diphenylprolinol silyl ether
organocatalyst

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-0037-1611644

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

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 B 0 is synthesized enantioselectively by using the present method as a key step. ",

keywords = "Michael reaction, asymmetric synthesis, diastereoselective reaction, diphenylprolinol silyl ether, organocatalyst",

author = "Yujiro Hayashi and Shunsuke Toda",

note = "Funding Information: JSPS KAKENHI grant number JP18H04641: Hybrid Catalysis for Enabling Molecular Synthesis on Demand, and The Uehara Memorial Foundation.JapanSocietyforthePromotionofScience(JP18H04641) Publisher Copyright: {\textcopyright} Georg Thieme Verlag.",

year = "2019",

doi = "10.1055/s-0037-1611644",

language = "English",

volume = "30",

pages = "442--448",

journal = "Synlett",

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publisher = "Georg Thieme Verlag",

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TY - JOUR

T1 - Asymmetric Synthesis of Chiral 1,3-Dimethyl Units Through a Double Michael Reaction of Nitromethane and Crotonaldehyde Catalyzed by Diphenylprolinol Silyl Ether

AU - Hayashi, Yujiro

AU - Toda, Shunsuke

N1 - Funding Information: JSPS KAKENHI grant number JP18H04641: Hybrid Catalysis for Enabling Molecular Synthesis on Demand, and The Uehara Memorial Foundation.JapanSocietyforthePromotionofScience(JP18H04641) Publisher Copyright: © Georg Thieme Verlag.

PY - 2019

Y1 - 2019

N2 - 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 B 0 is synthesized enantioselectively by using the present method as a key step.

AB - 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 B 0 is synthesized enantioselectively by using the present method as a key step.

KW - Michael reaction

KW - asymmetric synthesis

KW - diastereoselective reaction

KW - diphenylprolinol silyl ether

KW - organocatalyst

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DO - 10.1055/s-0037-1611644

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JO - Synlett

JF - Synlett

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ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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