Synthesis of Highly Substituted Pyridines through Copper-Catalyzed Condensation of Oximes and α,β-Unsaturated Imines

Wei Wen Tan; Yew Jin Ong; Naohiko Yoshikai

doi:10.1002/anie.201704378

Synthesis of Highly Substituted Pyridines through Copper-Catalyzed Condensation of Oximes and α,β-Unsaturated Imines

Wei Wen Tan, Yew Jin Ong, Naohiko Yoshikai

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

110 Citations (Scopus)

Abstract

A copper-catalyzed condensation reaction of oxime acetates and α,β-unsaturated ketimines to give pyridine derivatives is reported. The reaction features mild conditions, high functional-group compatibility, and high regioselectivity with respect to unsymmetrical oxime acetates, thus allowing the preparation of a wide range of polysubstituted pyridines, many of which are not readily accessible by conventional condensation methods.

Original language	English
Pages (from-to)	8240-8244
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	28
DOIs	https://doi.org/10.1002/anie.201704378
Publication status	Published - 2017 Jul 3
Externally published	Yes

Keywords

condensation
copper
oximes
pyridines
synthetic methods

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201704378

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abstract = "A copper-catalyzed condensation reaction of oxime acetates and α,β-unsaturated ketimines to give pyridine derivatives is reported. The reaction features mild conditions, high functional-group compatibility, and high regioselectivity with respect to unsymmetrical oxime acetates, thus allowing the preparation of a wide range of polysubstituted pyridines, many of which are not readily accessible by conventional condensation methods.",

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AU - Ong, Yew Jin

AU - Yoshikai, Naohiko

N1 - Funding Information: This work was supported by the Singapore Ministry of Education (RG3/15, RG114/15) and Nanyang Technological University. Publisher Copyright: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2017/7/3

Y1 - 2017/7/3

N2 - A copper-catalyzed condensation reaction of oxime acetates and α,β-unsaturated ketimines to give pyridine derivatives is reported. The reaction features mild conditions, high functional-group compatibility, and high regioselectivity with respect to unsymmetrical oxime acetates, thus allowing the preparation of a wide range of polysubstituted pyridines, many of which are not readily accessible by conventional condensation methods.

AB - A copper-catalyzed condensation reaction of oxime acetates and α,β-unsaturated ketimines to give pyridine derivatives is reported. The reaction features mild conditions, high functional-group compatibility, and high regioselectivity with respect to unsymmetrical oxime acetates, thus allowing the preparation of a wide range of polysubstituted pyridines, many of which are not readily accessible by conventional condensation methods.

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KW - copper

KW - oximes

KW - pyridines

KW - synthetic methods

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Synthesis of Highly Substituted Pyridines through Copper-Catalyzed Condensation of Oximes and α,β-Unsaturated Imines

Abstract

Keywords

ASJC Scopus subject areas

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