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Chem Commun (Camb). 2017 Feb 04;53(10):1657-1659. doi: 10.1039/c6cc09587a. Epub 2017 Jan 18.

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

Chemical communications (Cambridge, England)

Jun Li, Hai-Yan Tao, Chun-Jiang Wang

Affiliations

  1. College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China. [email protected].

PMID: 28098270 DOI: 10.1039/c6cc09587a

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.

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