Diarylprolinol-Mediated Asymmetric Direct Cross-Aldol Reaction of α,β-Unsaturated Aldehyde as an Electrophilic Aldehyde

Yujiro Hayashi; Kaito Nagai; Shigenobu Umemiya

doi:10.1002/asia.201901236

Diarylprolinol-Mediated Asymmetric Direct Cross-Aldol Reaction of α,β-Unsaturated Aldehyde as an Electrophilic Aldehyde

Yujiro Hayashi, Kaito Nagai, Shigenobu Umemiya

SCI - Chemistry

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

1 Citation (Scopus)

Abstract

The diarylprolinol-mediated asymmetric direct cross-aldol reaction of α,β-unsaturated aldehyde as an electrophilic aldehyde was developed. The reaction becomes accelerated by an acid when a carbonyl group is introduced at the γ-position of the α,β-unsaturated aldehyde. Synthetically useful γ,δ-unsaturated β-hydroxy aldehydes were obtained with high anti-selectivity and excellent enantioselectivity.

Original language	English
Pages (from-to)	4146-4149
Number of pages	4
Journal	Chemistry - An Asian Journal
Volume	14
Issue number	23
DOIs	https://doi.org/10.1002/asia.201901236
Publication status	Published - 2019 Dec 2

Keywords

aldehydes
aldol reaction
allyl alcohol
asymmetric synthesis
organocatalysis

ASJC Scopus subject areas

Biochemistry
Organic Chemistry

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title = "Diarylprolinol-Mediated Asymmetric Direct Cross-Aldol Reaction of α,β-Unsaturated Aldehyde as an Electrophilic Aldehyde",

abstract = "The diarylprolinol-mediated asymmetric direct cross-aldol reaction of α,β-unsaturated aldehyde as an electrophilic aldehyde was developed. The reaction becomes accelerated by an acid when a carbonyl group is introduced at the γ-position of the α,β-unsaturated aldehyde. Synthetically useful γ,δ-unsaturated β-hydroxy aldehydes were obtained with high anti-selectivity and excellent enantioselectivity.",

keywords = "aldehydes, aldol reaction, allyl alcohol, asymmetric synthesis, organocatalysis",

author = "Yujiro Hayashi and Kaito Nagai and Shigenobu Umemiya",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Number JP18H04380 and JP19H05630.",

year = "2019",

month = dec,

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doi = "10.1002/asia.201901236",

language = "English",

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journal = "Chemistry - An Asian Journal",

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T1 - Diarylprolinol-Mediated Asymmetric Direct Cross-Aldol Reaction of α,β-Unsaturated Aldehyde as an Electrophilic Aldehyde

AU - Hayashi, Yujiro

AU - Nagai, Kaito

AU - Umemiya, Shigenobu

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Number JP18H04380 and JP19H05630.

PY - 2019/12/2

Y1 - 2019/12/2

N2 - The diarylprolinol-mediated asymmetric direct cross-aldol reaction of α,β-unsaturated aldehyde as an electrophilic aldehyde was developed. The reaction becomes accelerated by an acid when a carbonyl group is introduced at the γ-position of the α,β-unsaturated aldehyde. Synthetically useful γ,δ-unsaturated β-hydroxy aldehydes were obtained with high anti-selectivity and excellent enantioselectivity.

AB - The diarylprolinol-mediated asymmetric direct cross-aldol reaction of α,β-unsaturated aldehyde as an electrophilic aldehyde was developed. The reaction becomes accelerated by an acid when a carbonyl group is introduced at the γ-position of the α,β-unsaturated aldehyde. Synthetically useful γ,δ-unsaturated β-hydroxy aldehydes were obtained with high anti-selectivity and excellent enantioselectivity.

KW - aldehydes

KW - aldol reaction

KW - allyl alcohol

KW - asymmetric synthesis

KW - organocatalysis

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