Issue 9, 2014

Copper(i)-catalyzed enantioselective hydroboration of cyclopropenes: facile synthesis of optically active cyclopropylboronates

Abstract

Copper(I)-catalyzed enantioselective hydroboration of 3-aryl substituted cyclopropene-3-carboxylate is described, providing chiral cyclopropylboronates with excellent enantioselectivities (89–95% ee) in moderate to high yields (55–86%). The non-directing effect of the ester group was observed, and the reaction proceeded with solely trans-selectivity. The chiral boronates could be conveniently converted into chiral 1,2-diaryl substituted cyclopropane derivatives.

Graphical abstract: Copper(i)-catalyzed enantioselective hydroboration of cyclopropenes: facile synthesis of optically active cyclopropylboronates

Supplementary files

Article information

Article type
Research Article
Submitted
28 may 2014
Accepted
05 sen 2014
First published
10 sen 2014

Org. Chem. Front., 2014,1, 1116-1122

Copper(I)-catalyzed enantioselective hydroboration of cyclopropenes: facile synthesis of optically active cyclopropylboronates

B. Tian, Q. Liu, X. Tong, P. Tian and G. Lin, Org. Chem. Front., 2014, 1, 1116 DOI: 10.1039/C4QO00157E

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements