Stereochemistry of the reaction of Si–phenyl silenes with butadienes: elaboration of the silacycloadducts to provide a novel route to substituted lactones†,10.1039/B404175E

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Stereochemistry of the reaction of Si–phenyl silenes with butadienes: elaboration of the silacycloadducts to provide a novel route to substituted lactones†

Mahesh J. Sanganee,Patrick G. Steel,Daniel K. Whelligan

Organic & Biomolecular Chemistry Pub Date : 07/29/2004 00:00:00 , DOI:10.1039/B404175E

Abstract

Silenes generated through a silyl-modified Peterson olefination procedure can be trapped with a range of alkyl butadienes via a [4 + 2] cycloaddition pathway to afford silacycles accompanied by variable amounts of competing ene, [2 + 2] and silene dimer by-products. The silacycles are formed with good chemo- and stereo-selectivity and provide access to diols and lactones via a phenyl-triggered Fleming–Tamao oxidation.