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Cooperative Brønsted acid-type organocatalysis: alcoholysis of styrene oxides.

Organic letters (2008-03-28)
Torsten Weil, Mike Kotke, Christian M Kleiner, Peter R Schreiner
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 beta-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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
2-Methyl-2-butanol, anhydrous, ≥99%