Catalytic enantioselective [2,3]-rearrangements of amine N-oxides

Hongli Bao; Xiangbing Qi; Uttam K. Tambar

doi:10.1021/ja110500m

Catalytic enantioselective [2,3]-rearrangements of amine N-oxides

Hongli Bao, Xiangbing Qi, Uttam K. Tambar

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40 Scopus citations

Abstract

The first Pd-catalyzed enantioselective [2,3]-rearrangement of allylic amine N-oxides is described, which formally represents an asymmetric Meisenheimer rearrangement. The mild reaction conditions enable the synthesis of chiral nonracemic aliphatic allylic alcohol derivatives with reactive functional groups. On the basis of preliminary studies, a cyclization-mediated mechanism is proposed.

Original language	English (US)
Pages (from-to)	1206-1208
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	133
Issue number	5
DOIs	https://doi.org/10.1021/ja110500m
State	Published - Feb 9 2011

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja110500m

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abstract = "The first Pd-catalyzed enantioselective [2,3]-rearrangement of allylic amine N-oxides is described, which formally represents an asymmetric Meisenheimer rearrangement. The mild reaction conditions enable the synthesis of chiral nonracemic aliphatic allylic alcohol derivatives with reactive functional groups. On the basis of preliminary studies, a cyclization-mediated mechanism is proposed.",

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AB - The first Pd-catalyzed enantioselective [2,3]-rearrangement of allylic amine N-oxides is described, which formally represents an asymmetric Meisenheimer rearrangement. The mild reaction conditions enable the synthesis of chiral nonracemic aliphatic allylic alcohol derivatives with reactive functional groups. On the basis of preliminary studies, a cyclization-mediated mechanism is proposed.

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Catalytic enantioselective [2,3]-rearrangements of amine N-oxides

Abstract

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