Intermediate as catalyst: Catalytic asymmetric conjugate addition of nitroalkanes to α,β-unsaturated thioamides

Takanori Ogawa; Shinsuke Mouri; Ryo Yazaki; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1021/ol202898e

Intermediate as catalyst: Catalytic asymmetric conjugate addition of nitroalkanes to α,β-unsaturated thioamides

Takanori Ogawa, Shinsuke Mouri, Ryo Yazaki, Naoya Kumagai, Masakatsu Shibasaki

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

28 Citations (Scopus)

Abstract

Catalytic asymmetric conjugate addition of nitroalkanes to α,β-unsaturated thioamides is promoted by a mesitylcopper/(R)-DTBM- Segphos precatalyst, affording γ-nitrothioamides in moderate to high syn-selectivity and excellent enantioselectivity. The intermediate Cu-thioamide enolate functions as a soft Lewis acid/hard Brønsted base cooperative catalyst to drive the catalytic cycle efficiently under proton transfer conditions.

Original language	English
Pages (from-to)	110-113
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	1
DOIs	https://doi.org/10.1021/ol202898e
Publication status	Published - 2012 Jan 6
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol202898e

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AU - Ogawa, Takanori

AU - Mouri, Shinsuke

AU - Yazaki, Ryo

AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

PY - 2012/1/6

Y1 - 2012/1/6

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AB - Catalytic asymmetric conjugate addition of nitroalkanes to α,β-unsaturated thioamides is promoted by a mesitylcopper/(R)-DTBM- Segphos precatalyst, affording γ-nitrothioamides in moderate to high syn-selectivity and excellent enantioselectivity. The intermediate Cu-thioamide enolate functions as a soft Lewis acid/hard Brønsted base cooperative catalyst to drive the catalytic cycle efficiently under proton transfer conditions.

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Intermediate as catalyst: Catalytic asymmetric conjugate addition of nitroalkanes to α,β-unsaturated thioamides

Abstract

ASJC Scopus subject areas

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