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Regioselective SN2 Opening of Vinylic Epoxides with Trialkylzincates and Trialkylaluminates

✍ Scribed by Olivier Equey; Emmanuel Vrancken; Alexandre Alexakis

Publisher
John Wiley and Sons
Year
2004
Tongue
English
Weight
151 KB
Volume
2004
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

The use of trialkylorganozincates and tetraalkylaluminates allows regioselective S~N~2 nucleophilic opening of vinylic epoxides. The reaction occurs with an anti‐substitution pattern and can be applied to a wide range of substrates. We also show that the solvent and the structure of the epoxide have an influence on the substitution products’ ratio. (Β© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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## Ring opening reactions O 0132 Regioselective and Divergent Opening of Vinyl Epoxides with Ethoxyacetylene. -A divergent protocol for regioselective alkynylations of vinyl epoxides (I) and (IV) is described. The combination of lithium ethoxyacetylide (II) and BF3β€’Et2O gives SN2 displacement, cf