Issue 10, 2017

Copper(i)/TF-BiphamPhos catalyzed asymmetric nitroso Diels–Alder reaction

Abstract

A highly efficient enantioselective nitroso Diels–Alder reaction of 6-methyl-2-nitroso pyridine with various 1,3-dienes was successfully developed using a Cu(I)/(S)–TF-BiphamPhos complex as the catalyst. For most of the cyclic dienes, synthetically important heterocyclic 3,6-dihydro-1,2-oxazines were obtained in high yields with excellent regio-, diastereo- and enantioselectivities. Acyclic 2-silyloxy-1,3-diene also worked well in the reaction.

Graphical abstract: Copper(i)/TF-BiphamPhos catalyzed asymmetric nitroso Diels–Alder reaction

Supplementary files

Article information

Article type
Communication
Submitted
02 Dec 2016
Accepted
06 Jan 2017
First published
10 Jan 2017

Chem. Commun., 2017,53, 1657-1659

Copper(I)/TF-BiphamPhos catalyzed asymmetric nitroso Diels–Alder reaction

J. Li, H. Tao and C. Wang, Chem. Commun., 2017, 53, 1657 DOI: 10.1039/C6CC09587A

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