Ned Porter
Faculty Member
Last active: 5/29/2014

Diastereoselective free radical halogenation, azidation, and rearrangement of beta-silyl Barton esters.

Masterson DS, Porter NA
Org Lett. 2002 4 (24): 4253-6

PMID: 12443071 · DOI:10.1021/ol0268182

[reaction: see text] Barton esters of beta-silylcarboxylic acids were decomposed by photolysis alone in organic solvents or in the presence of ethanesulfonyl azide or bromotrichloromethane. Products of the reaction, beta-silylthiopyridyl ethers, beta-silyl azides, or alkenes, were formed with significant control of stereochemistry.

MeSH Terms (8)

Azides Esters Free Radicals Halogens Molecular Conformation Molecular Structure Photolysis Stereoisomerism

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