Diastereoselective synthesis of trisubstituted olefins using a silicon-tether ring-closing metathesis strategy

Wittmann, S., Tiniakos, A. F. and Prunet, J. (2020) Diastereoselective synthesis of trisubstituted olefins using a silicon-tether ring-closing metathesis strategy. Organic and Biomolecular Chemistry, pp. 2297-2306. (doi: 10.1039/C9OB02563D)

Abstract

The diastereoselective synthesis of trisubstituted olefins with concomitant C–C bond formation is still a difficult challenge, and olefin metathesis reactions for the formation of such alkenes are usually not high yielding or/and diastereoselective. Herein we report an efficient and diastereoselective synthesis of trisubstituted olefins flanked by an allylic alcohol, by a silicon-tether ring-closing metathesis strategy. Both E- and Z-trisubstituted alkenes were synthesised, depending on the method employed to cleave the silicon tether. Furthermore, this methodology features a novel Peterson olefination for the synthesis of allyldimethylsilanes. These versatile intermediates were also converted into the corresponding allylchlorodimethylsilanes, which are not easily accessible in high yields by other methods.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Tiniakos, Mr Alexander and Wittmann, Mr Stephane and Prunet, Dr Joelle
• Authors: Wittmann, S., Tiniakos, A. F., and Prunet, J.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Organic and Biomolecular Chemistry
• Publisher: Royal Society of Chemistry
• ISSN: 1477-0520
• ISSN (Online): 1477-0539
• Published Online: 05 March 2020
• Copyright Holders: Copyright © 2020 The Royal Society of Chemistry
• First Published: First published in Organic and Biomolecular Chemistry 2020 18:2297-2306
• Publisher Policy: Reproduced under a Creative Commons licence

Project Code	Award No	Project Name	Principal Investigator	Funder's Name	Funder Ref	Lead Dept
190906		EPSRC 2015 DTP	Mary Beth Kneafsey	Engineering and Physical Sciences Research Council (EPSRC)	EP/M508056/1	Research and Innovation Services