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

Abstract

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.

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Title:

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

Creators:

Gill, Duncan M., Taylor, Nicholas H. and Thomas, Eric J.

Identification Number:

10.1016/j.tet.2011.03.113

Official URL:

http://dx.doi.org/10.1016/j.tet.2011.03.113

Date:

16 April 2011

Subjects:

Q Science > QD Chemistry

Schools:

School of Applied Sciences

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Item Type:

Article

Depositing User:

Date Deposited:

01 Jun 2012 09:20

Revision:

18

Last Modified:

28 Aug 2021 20:46

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