Direct catalytic asymmetric mannich-type reaction of thioamides

Yuta Suzuki; Ryo Yazaki; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1002/anie.200901588

Direct catalytic asymmetric mannich-type reaction of thioamides

Yuta Suzuki, Ryo Yazaki, Naoya Kumagai, Masakatsu Shibasaki

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

59 Citations (Scopus)

Abstract

Taking the reins: The title transformation of thioamides and N-diphenylphosphinoyl imines is described. By harnessing the power of cooperative catalysis between a soft Lewis acid and a hard Brønsted base, thioamide carbon pronucleophiles can furnish Mannich products (see scheme). Divergent transformation of the thioamide functionality highlights the utility of this methodology.

Original language	English
Pages (from-to)	5026-5029
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	48
Issue number	27
DOIs	https://doi.org/10.1002/anie.200901588
Publication status	Published - 2009 Jun 22
Externally published	Yes

Keywords

Asymmetric catalysis
Copper
Mannich reactions
Proton transfer
Thioamides

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.200901588

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AU - Suzuki, Yuta

AU - Yazaki, Ryo

AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

PY - 2009/6/22

Y1 - 2009/6/22

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AB - Taking the reins: The title transformation of thioamides and N-diphenylphosphinoyl imines is described. By harnessing the power of cooperative catalysis between a soft Lewis acid and a hard Brønsted base, thioamide carbon pronucleophiles can furnish Mannich products (see scheme). Divergent transformation of the thioamide functionality highlights the utility of this methodology.

KW - Asymmetric catalysis

KW - Copper

KW - Mannich reactions

KW - Proton transfer

KW - Thioamides

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Direct catalytic asymmetric mannich-type reaction of thioamides

Abstract

Keywords

ASJC Scopus subject areas

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