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.; Steel, P.G.; Whelligan, D.K.

doi:10.1039/b404175e

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.; Steel, P.G.; Whelligan, D.K.

Authors

M.J. Sanganee

Professor Patrick Steel p.g.steel@durham.ac.uk
Professor

D.K. Whelligan

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.

Citation

Sanganee, M., Steel, P., & Whelligan, D. (2004). Stereochemistry of the reaction of Si-phenyl silenes with butadienes: elaboration of the silacycloadducts to provide a novel route to substituted lactones. Organic and Biomolecular Chemistry, 2(16), 2393-2402. https://doi.org/10.1039/b404175e

Journal Article Type	Article
Publication Date	Jul 1, 2004
Deposit Date	May 10, 2007
Journal	Organic and Biomolecular Chemistry
Print ISSN	1477-0520
Electronic ISSN	1477-0539
Publisher	Royal Society of Chemistry
Peer Reviewed	Peer Reviewed
Volume	2
Issue	16
Pages	2393-2402
DOI	https://doi.org/10.1039/b404175e