Enantioselective 1,4-addition of unmodified ketone catalyzed by a bimetallic Zn-Zn-linked-binol complex

Naoya Kumagai; Shigeki Matsunaga; Masakatsu Shibasaki

doi:10.1021/ol016981h

Enantioselective 1,4-addition of unmodified ketone catalyzed by a bimetallic Zn-Zn-linked-binol complex

Naoya Kumagai, Shigeki Matsunaga, Masakatsu Shibasaki

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

66 Citations (Scopus)

Abstract

(Matrix Presented) 1,4-Addition (Michael addition) of 2-hydroxy-2′-methoxyacetophenone (2) to various αβ-unsaturated ketones was efficiently promoted by a bimetallic Zn-Zn-linked-BINOL complex 3 with good yield (up to 90%) and excellent enantiomeric excess (up to 99% ee). The resulting 2-hydroxy-1,5-diketones were successfully converted to synthetically more versatile esters and amides.

Original language	English
Pages (from-to)	4251-4254
Number of pages	4
Journal	Organic Letters
Volume	3
Issue number	26
DOIs	https://doi.org/10.1021/ol016981h
Publication status	Published - 2001 Dec 27
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol016981h

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author = "Naoya Kumagai and Shigeki Matsunaga and Masakatsu Shibasaki",

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AU - Matsunaga, Shigeki

AU - Shibasaki, Masakatsu

PY - 2001/12/27

Y1 - 2001/12/27

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AB - (Matrix Presented) 1,4-Addition (Michael addition) of 2-hydroxy-2′-methoxyacetophenone (2) to various αβ-unsaturated ketones was efficiently promoted by a bimetallic Zn-Zn-linked-BINOL complex 3 with good yield (up to 90%) and excellent enantiomeric excess (up to 99% ee). The resulting 2-hydroxy-1,5-diketones were successfully converted to synthetically more versatile esters and amides.

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Enantioselective 1,4-addition of unmodified ketone catalyzed by a bimetallic Zn-Zn-linked-binol complex

Abstract

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