Cooperative Brønsted Acid-Type Organocatalysis: Alcoholysis of Styrene Oxides
- 27 March 2008
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 10 (8) , 1513-1516
- https://doi.org/10.1021/ol800149y
Abstract
We present a mild and efficient method for the completely regioselective alcoholysis of styrene oxides utilizing a cooperative Brønsted acid-type organocatalytic system comprised of mandelic acid (1 mol %) and N,N‘-bis-[3,5-bis-(trifluoromethyl)phenyl]-thiourea (1 mol %). Various styrene oxides are readily transformed into their corresponding β-alkoxy alcohols in good to excellent yields at full conversion. Simple aliphatic and sterically demanding, as well as unsaturated and acid-sensitive alcohols can be employed.Keywords
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