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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.

Sanganee, M. J. and Steel, P. G. and Whelligan, D. K. (2004) 'Stereochemistry of the reaction of Si-phenyl silenes with butadienes : elaboration of the silacycloadducts to provide a novel route to substituted lactones.', Organic & biomolecular chemistry., 2 (16). pp. 2393-2402.

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.

Item Type:Article
Full text:Full text not available from this repository.
Publisher Web site:http://dx.doi.org/ 10.1039/B404175E
Record Created:10 May 2007
Last Modified:08 Apr 2009 16:31

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