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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, MJ, Steel, PG and Whelligan, DK (2004) Stereochemistry of the reaction of Si-phenyl silenes with butadienes: elaboration of the silacycloadducts to provide a novel route to substituted lactones. Org Biomol Chem, 2 (16). pp. 2393-2402.

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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
Authors :
NameEmailORCID
Sanganee, MJUNSPECIFIEDUNSPECIFIED
Steel, PGUNSPECIFIEDUNSPECIFIED
Whelligan, DKd.whelligan@surrey.ac.ukUNSPECIFIED
Date : 21 August 2004
Identification Number : https://doi.org/10.1039/B404175E
Uncontrolled Keywords : Acylation, Butadienes, Lactones, Magnetic Resonance Spectroscopy, Molecular Structure, Silene, Silicon, Stereoisomerism
Depositing User : Symplectic Elements
Date Deposited : 17 May 2017 12:07
Last Modified : 17 May 2017 15:01
URI: http://epubs.surrey.ac.uk/id/eprint/834108

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