Direct Catalytic Asymmetric Aldol Reaction of α-Alkylamides

Zijian Liu; Toshifumi Takeuchi; Roman Pluta; Fernando Arteaga Arteaga; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1021/acs.orglett.6b03890

Direct Catalytic Asymmetric Aldol Reaction of α-Alkylamides

Zijian Liu, Toshifumi Takeuchi, Roman Pluta, Fernando Arteaga Arteaga, Naoya Kumagai, Masakatsu Shibasaki

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

29 Citations (Scopus)

Abstract

A catalytic asymmetric aldol reaction directly employing amides as latent enolates has remained elusive because of the resistance of amides to enolization. A direct aldol reaction of α-alkylamides without any electron-withdrawing group harnessed by specific activation of 7-azaindoline amides under soft Lewis acid/Brønsted base cooperative catalysis is reported. Diastereo- and enantioselective coupling with ynals and aromatic aldehydes as well as divergent functional group interconversion of the amide provided expeditious access to a variety of aliphatic and aromatic chiral building blocks.

Original language	English
Pages (from-to)	710-713
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	3
DOIs	https://doi.org/10.1021/acs.orglett.6b03890
Publication status	Published - 2017 Feb 3
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "A catalytic asymmetric aldol reaction directly employing amides as latent enolates has remained elusive because of the resistance of amides to enolization. A direct aldol reaction of α-alkylamides without any electron-withdrawing group harnessed by specific activation of 7-azaindoline amides under soft Lewis acid/Br{\o}nsted base cooperative catalysis is reported. Diastereo- and enantioselective coupling with ynals and aromatic aldehydes as well as divergent functional group interconversion of the amide provided expeditious access to a variety of aliphatic and aromatic chiral building blocks.",

author = "Zijian Liu and Toshifumi Takeuchi and Roman Pluta and {Arteaga Arteaga}, Fernando and Naoya Kumagai and Masakatsu Shibasaki",

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AU - Liu, Zijian

AU - Takeuchi, Toshifumi

AU - Pluta, Roman

AU - Arteaga Arteaga, Fernando

AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

PY - 2017/2/3

Y1 - 2017/2/3

N2 - A catalytic asymmetric aldol reaction directly employing amides as latent enolates has remained elusive because of the resistance of amides to enolization. A direct aldol reaction of α-alkylamides without any electron-withdrawing group harnessed by specific activation of 7-azaindoline amides under soft Lewis acid/Brønsted base cooperative catalysis is reported. Diastereo- and enantioselective coupling with ynals and aromatic aldehydes as well as divergent functional group interconversion of the amide provided expeditious access to a variety of aliphatic and aromatic chiral building blocks.

AB - A catalytic asymmetric aldol reaction directly employing amides as latent enolates has remained elusive because of the resistance of amides to enolization. A direct aldol reaction of α-alkylamides without any electron-withdrawing group harnessed by specific activation of 7-azaindoline amides under soft Lewis acid/Brønsted base cooperative catalysis is reported. Diastereo- and enantioselective coupling with ynals and aromatic aldehydes as well as divergent functional group interconversion of the amide provided expeditious access to a variety of aliphatic and aromatic chiral building blocks.

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Direct Catalytic Asymmetric Aldol Reaction of α-Alkylamides

Abstract

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