Diphenylprolinol silyl ether catalysis in an asymmetric formal carbo [3 + 3] cycloaddition reaction via a domino michael/knoevenagel condensation

Yujiro Hayashi; Maya Toyoshima; Hiroaki Gotoh; Hayato Ishikawa

doi:10.1021/ol802330h

Diphenylprolinol silyl ether catalysis in an asymmetric formal carbo [3 + 3] cycloaddition reaction via a domino michael/knoevenagel condensation

Yujiro Hayashi, Maya Toyoshima, Hiroaki Gotoh, Hayato Ishikawa

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

105 Citations (Scopus)

Abstract

Diphenylprolinol silyl ether was found to catalyze the formal carbo [3 + 3] cycloaddition reaction through the domino reaction via the Michael reaction, followed by Knoevenagel condensation of the α, β-unsaturated aldehyde and dimethyl 3-oxopentanedioate, affording substituted cyclohexenone derivatives with excellent enantioselectivity.

Original language	English
Pages (from-to)	45-48
Number of pages	4
Journal	Organic letters
Volume	11
Issue number	1
DOIs	https://doi.org/10.1021/ol802330h
Publication status	Published - 2009 Jan 1
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol802330h

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abstract = "Diphenylprolinol silyl ether was found to catalyze the formal carbo [3 + 3] cycloaddition reaction through the domino reaction via the Michael reaction, followed by Knoevenagel condensation of the α, β-unsaturated aldehyde and dimethyl 3-oxopentanedioate, affording substituted cyclohexenone derivatives with excellent enantioselectivity.",

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AU - Gotoh, Hiroaki

AU - Ishikawa, Hayato

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AB - Diphenylprolinol silyl ether was found to catalyze the formal carbo [3 + 3] cycloaddition reaction through the domino reaction via the Michael reaction, followed by Knoevenagel condensation of the α, β-unsaturated aldehyde and dimethyl 3-oxopentanedioate, affording substituted cyclohexenone derivatives with excellent enantioselectivity.

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Diphenylprolinol silyl ether catalysis in an asymmetric formal carbo [3 + 3] cycloaddition reaction via a domino michael/knoevenagel condensation

Abstract

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