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Synthesis of 2,6-cis-disubstituted 4-methylenetetrahydropyrans by oxy-Michael addition

Gill, Duncan M., Taylor, Nicholas H. and Thomas, Eric J. (2011) Synthesis of 2,6-cis-disubstituted 4-methylenetetrahydropyrans by oxy-Michael addition. Tetrahedron, 67 (27-28). pp. 5034-5045. ISSN 0040-4020

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The combination of an ‘ene’ reaction between a 2-(2-trialkylsilyloxyalkyl)prop-2-enyl(trimethyl)silane and an alk-1-yn-3-one mediated by zinc(II) iodide, and an intramolecular oxy-Michael reaction, provides an efficient synthesis of cis-2,6-disubstituted 4-methylenetetrahydropyrans of interest in the context of a synthesis of bryostatins. The stereoselective formation of (E)-vinylsilanes in the ‘ene’ reaction is of interest.

Item Type: Article
Subjects: Q Science > QD Chemistry
Schools: School of Applied Sciences
Depositing User: Duncan Gill
Date Deposited: 01 Jun 2012 09:20
Last Modified: 28 Aug 2021 20:46


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