94956-84-0Relevant articles and documents
Synthesis of 2,6-cis-disubstituted 4-methylenetetrahydropyrans by oxy-Michael addition
Gill, Duncan,Taylor, Nicholas H.,Thomas, Eric J.
experimental part, p. 5034 - 5045 (2011/08/06)
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.