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Regioselective and Divergent Opening of Vinyl Epoxides with Ethoxyacetylene.

✍ Scribed by Per Restorp; Peter Somfai

Publisher
John Wiley and Sons
Year
2005
Weight
23 KB
Volume
36
Category
Article
ISSN
0931-7597

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✦ Synopsis

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. formation of (III) and (V). Alkynylalanes derived from (II) afford the SN2 ' adducts (VI). Compounds (III) can be transformed to Ξ²,Ξ³-disubstituted Ξ³-butyro-

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Regioselective SN2 Opening of Vinylic Ep
Regioselective SN2 Opening of Vinylic Epoxides with Trialkylzincates and Trialkylaluminates
✍ Olivier Equey; Emmanuel Vrancken; Alexandre Alexakis πŸ“‚ Article πŸ“… 2004 πŸ› John Wiley and Sons 🌐 English βš– 151 KB πŸ‘ 1 views

## 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