Syn-selective kobayashi aldol reaction using acetals

Hiroyuki Tsukada; Yuki Mukaeda; Seijiro Hosokawa

doi:10.1021/ol303519y

Syn-selective kobayashi aldol reaction using acetals

Hiroyuki Tsukada, Yuki Mukaeda, Seijiro Hosokawa^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

34 Citations (Scopus)

Abstract

The Kobayashi aldol reaction has been used to construct anti-aldol products by remote stereoinduction. Since the product of the Kobayashi aldol reaction has a typical polyketide structure, this reaction has been applied to the total synthesis of natural products. By varying this reaction, it was found that the reaction with acetals in the presence of Lewis acid proceeded to give syn adducts in high stereoselectivity. This is the first example of the stereoselective reaction of the chiral dienol ether and acetals.

Original language	English
Pages (from-to)	678-681
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	3
DOIs	https://doi.org/10.1021/ol303519y
Publication status	Published - 2013 Feb 1

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol303519y

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N2 - The Kobayashi aldol reaction has been used to construct anti-aldol products by remote stereoinduction. Since the product of the Kobayashi aldol reaction has a typical polyketide structure, this reaction has been applied to the total synthesis of natural products. By varying this reaction, it was found that the reaction with acetals in the presence of Lewis acid proceeded to give syn adducts in high stereoselectivity. This is the first example of the stereoselective reaction of the chiral dienol ether and acetals.

AB - The Kobayashi aldol reaction has been used to construct anti-aldol products by remote stereoinduction. Since the product of the Kobayashi aldol reaction has a typical polyketide structure, this reaction has been applied to the total synthesis of natural products. By varying this reaction, it was found that the reaction with acetals in the presence of Lewis acid proceeded to give syn adducts in high stereoselectivity. This is the first example of the stereoselective reaction of the chiral dienol ether and acetals.

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Syn-selective kobayashi aldol reaction using acetals

Abstract

ASJC Scopus subject areas

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