Issue 23, 2018

Copper-catalyzed enantioselective 1,2-borylation of 1,3-dienes

Abstract

A highly enantioselective Cu-catalyzed borylation of 2-substituted 1,3-dienes is reported. The use of a chiral phosphanamine ligand is essential in achieving high chemo-, regio-, diastereo- and enantioselectivity. It provides access to a variety of homoallylic boronates in consistently high yield and enantiomeric excess with 2-aryl and 2-heteroaryl 1,3-dienes as well as sterically demanding 2-alkyl 1,3-dienes. Preliminary investigations based on a non-linear effect study point to a mechanism involving more than one metal center.

Graphical abstract: Copper-catalyzed enantioselective 1,2-borylation of 1,3-dienes

Supplementary files

Article information

Article type
Edge Article
Submitted
04 Apr 2018
Accepted
22 May 2018
First published
23 May 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., 2018,9, 5284-5288

Copper-catalyzed enantioselective 1,2-borylation of 1,3-dienes

Y. Liu, D. Fiorito and C. Mazet, Chem. Sci., 2018, 9, 5284 DOI: 10.1039/C8SC01538D

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