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Updated: Apr 26, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Tandem Prins/pinacol reaction for the synthesis of oxaspiro[4.5]decan-1-one scaffolds
B V Subba Reddy1, S Gopal Reddy, M Ramana Reddy
1Natural Product Chemistry, Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad, 500607, India. basireddy@iict.res.in.
Abstract:
A novel Lewis acid catalyzed Prins/pinacol cascade process has been developed for the synthesis of 7-substituted-8-oxaspiro[4.5]decan-1-ones in good yields with excellent selectivity. This is the first example of the synthesis of oxaspirocycles from aldehydes and 1-(4-hydroxybut-1-en-2-yl)cyclobutanol through a cascade of Prins/pinacol rearrangement. This method is applicable to a wide range of aldehydes such as aromatic, aliphatic, heteroaromatic, and α,β-unsaturated aldehydes.
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