BF2OBn∙OEt2: A Novel Lewis Acid and its use in a Regio- and Stereo-selective Opening of Trisubstituted Epoxides and its Application Towards Amphidinolide C

Authors

Nicholas A. Morra
Brian Pagenkopf, University of Western OntarioFollow

Document Type

Article

Publication Date

12-10-2012

Journal

European Journal of Organic Chemistry

Volume

2013

Issue

4

First Page

756

Last Page

760

URL with Digital Object Identifier

http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201201331/abstract

Abstract

The generation of a new Lewis acid (BF2OBn·OEt2) has been reported, and its usefulness has been demonstrated in the regio- and stereoselective ring-opening of trisubstituted epoxides. This Lewis acid is one in a series of new Lewis acids generated from BF3·OEt2 that display varying levels of Lewis acidity. When paired with a modified Shi epoxidation protocol, highly functionalized propionate units, such as those found in a wide variety of natural products, can be accessed. In conjunction with a Mukaiyama oxidative cyclization employing our second generation catalyst Co(nmp)2, this procedure ultimately culminated in the shortest and highest yielding route towards the methyl-substituted trans-tetrahydrofuran (trans-THF) fragment present in amphidinolide C, C2, and F.

Notes

This is the peer reviewed version which has been published in final form at http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201201331/abstract. This article may be used for non-commercial purposes in accordance With Wiley-VCH Terms and Conditions for self-archiving".