The first organocatalytic carbonyl-ene reaction: isomerisation-free C-C bond formations catalysed by H-bonding thio-ureas.

Beilstein J Org Chem

School of Chemistry, University of St, Andrews, EaStCHEM, St, Andrews, Fife, KY16 9ST, UK.

Published: September 2007

Intramolecular carbonyl ene reactions of highly activated enophiles can be catalysed by H-bonding thio-ureas to give tertiary alcohols in high yields without extensive isomerisation side products. An asymmetric variant of this reaction was realised using a chiral thiourea but was limited by low enantioselectivity (up to 33% e.e.) and low turnover frequencies.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2176055PMC
http://dx.doi.org/10.1186/1860-5397-3-24DOI Listing

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