Issue 12, 2016

Highly diastereoselective approach to methylenecyclopropanes via boron-homologation/allylboration sequences

Abstract

A simple and efficient diastereoselective synthesis of methylenecyclopropanes is described, in which boron-homologation and allylboration are merged into a one-pot process, starting from in situ generated cyclopropenyllithium species. This unprecedented methodology opens a new route to strained alkylidenecycloalkanes containing a quaternary stereocenter, in high yields and excellent diastereomeric ratios.

Graphical abstract: Highly diastereoselective approach to methylenecyclopropanes via boron-homologation/allylboration sequences

Supplementary files

Article information

Article type
Communication
Submitted
01 Dec 2015
Accepted
04 Jan 2016
First published
04 Jan 2016
This article is Open Access
Creative Commons BY license

Chem. Commun., 2016,52, 2529-2532

Author version available

Highly diastereoselective approach to methylenecyclopropanes via boron-homologation/allylboration sequences

A. N. Baumann, A. Music, K. Karaghiosoff and D. Didier, Chem. Commun., 2016, 52, 2529 DOI: 10.1039/C5CC09904H

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