Issue 6, 2019

Enantioselective and site-specific copper-catalyzed reductive allyl–allyl cross-coupling of allenes

Abstract

A copper-catalyzed asymmetric reductive allyl–allyl cross-coupling reaction of allenes with allylic phosphates wherein allenes were used as allylmetal surrogates has been achieved for the first time. This protocol provides an efficient and straightforward route to optically active 1,5-dienes in a highly enantioselective and site-specific fashion. Furthermore, all-carbon quaternary stereogenic centers could also be constructed with this protocol. The versatility of the products is demonstrated through a diverse array of further transformations of the enantioenriched 1,5-dienes.

Graphical abstract: Enantioselective and site-specific copper-catalyzed reductive allyl–allyl cross-coupling of allenes

Supplementary files

Article information

Article type
Edge Article
Submitted
10 Oct 2018
Accepted
03 Dec 2018
First published
04 Dec 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 1802-1806

Enantioselective and site-specific copper-catalyzed reductive allyl–allyl cross-coupling of allenes

G. Xu, B. Fu, H. Zhao, Y. Li, G. Zhang, Y. Wang, T. Xiong and Q. Zhang, Chem. Sci., 2019, 10, 1802 DOI: 10.1039/C8SC04505D

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