One-pot synthesis of chiral α-substituted β,γ-epoxy aldehyde derivatives through an asymmetric aldol reaction of chloroacetaldehyde

Yujiro Hayashi; Yusuke Yasui; Tsuyoshi Kawamura; Masahiro Kojima; Hayato Ishikawa

doi:10.1002/anie.201005577

One-pot synthesis of chiral α-substituted β,γ-epoxy aldehyde derivatives through an asymmetric aldol reaction of chloroacetaldehyde

Yujiro Hayashi, Yusuke Yasui, Tsuyoshi Kawamura, Masahiro Kojima, Hayato Ishikawa

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

43 Citations (Scopus)

Abstract

Water is welcome! Chiral α-substituted β,γ-epoxides have been prepared in good yields and with excellent enantioselectivities in a one-pot synthetic procedure. The key reaction of this process, which involves a series of uninterrupted sequential reactions, is an asymmetric aldol reaction of aqueous chloroacetaldehyde mediated by a diarylprolinol derivative (see scheme).

Original language	English
Pages (from-to)	2804-2807
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	12
DOIs	https://doi.org/10.1002/anie.201005577
Publication status	Published - 2011 Mar 14
Externally published	Yes

Keywords

aldol reaction
asymmetric synthesis
diarylprolinol derivatives
epoxidation
organocatalysis

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201005577

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AU - Hayashi, Yujiro

AU - Yasui, Yusuke

AU - Kawamura, Tsuyoshi

AU - Kojima, Masahiro

AU - Ishikawa, Hayato

PY - 2011/3/14

Y1 - 2011/3/14

N2 - Water is welcome! Chiral α-substituted β,γ-epoxides have been prepared in good yields and with excellent enantioselectivities in a one-pot synthetic procedure. The key reaction of this process, which involves a series of uninterrupted sequential reactions, is an asymmetric aldol reaction of aqueous chloroacetaldehyde mediated by a diarylprolinol derivative (see scheme).

AB - Water is welcome! Chiral α-substituted β,γ-epoxides have been prepared in good yields and with excellent enantioselectivities in a one-pot synthetic procedure. The key reaction of this process, which involves a series of uninterrupted sequential reactions, is an asymmetric aldol reaction of aqueous chloroacetaldehyde mediated by a diarylprolinol derivative (see scheme).

KW - aldol reaction

KW - asymmetric synthesis

KW - diarylprolinol derivatives

KW - epoxidation

KW - organocatalysis

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One-pot synthesis of chiral α-substituted β,γ-epoxy aldehyde derivatives through an asymmetric aldol reaction of chloroacetaldehyde

Abstract

Keywords

ASJC Scopus subject areas

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