A designed amide as an aldol donor in the direct catalytic asymmetric aldol reaction

Karin Weidner; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1002/anie.201403118

A designed amide as an aldol donor in the direct catalytic asymmetric aldol reaction

Karin Weidner, Naoya Kumagai, Masakatsu Shibasaki

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

48 Citations (Scopus)

Abstract

The direct catalytic asymmetric aldol reaction offers efficient access to β-hydroxy carbonyl entities. Described is a robust direct catalytic asymmetric aldol reaction of α-sulfanyl 7-azaindolinylamide, thus affording both aromatic and aliphatic β-hydroxy amides with high ee values. The design of this transformation features a cooperative interplay of a soft and a hard Lewis acid, which together facilitate the challenging chemoselective enolization by a hard Brønsted base.

Original language	English
Pages (from-to)	6150-6154
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	53
Issue number	24
DOIs	https://doi.org/10.1002/anie.201403118
Publication status	Published - 2014 Jun 10
Externally published	Yes

Keywords

aldol reaction
amides
asymmetric catalysis
silver
synthetic methods

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201403118

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AU - Kumagai, Naoya

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AB - The direct catalytic asymmetric aldol reaction offers efficient access to β-hydroxy carbonyl entities. Described is a robust direct catalytic asymmetric aldol reaction of α-sulfanyl 7-azaindolinylamide, thus affording both aromatic and aliphatic β-hydroxy amides with high ee values. The design of this transformation features a cooperative interplay of a soft and a hard Lewis acid, which together facilitate the challenging chemoselective enolization by a hard Brønsted base.

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KW - amides

KW - asymmetric catalysis

KW - silver

KW - synthetic methods

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A designed amide as an aldol donor in the direct catalytic asymmetric aldol reaction

Abstract

Keywords

ASJC Scopus subject areas

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