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Issue 12, 2020
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Diastereoselective synthesis of trisubstituted olefins using a silicon-tether ring-closing metathesis strategy

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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.

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

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Supplementary files

Article information


Submitted
30 Nov 2019
Accepted
04 Mar 2020
First published
05 Mar 2020

This article is Open Access

Org. Biomol. Chem., 2020,18, 2297-2306
Article type
Paper

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

S. Wittmann, A. F. Tiniakos and J. Prunet, Org. Biomol. Chem., 2020, 18, 2297
DOI: 10.1039/C9OB02563D

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