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Issue 37, 2014
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Tandem Prins/pinacol reaction for the synthesis of oxaspiro[4.5]decan-1-one scaffolds

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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.

Graphical abstract: Tandem Prins/pinacol reaction for the synthesis of oxaspiro[4.5]decan-1-one scaffolds

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Publication details

The article was received on 09 Jun 2014, accepted on 28 Jul 2014 and first published on 28 Jul 2014


Article type: Paper
DOI: 10.1039/C4OB01188K
Citation: Org. Biomol. Chem., 2014,12, 7257-7260
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    Tandem Prins/pinacol reaction for the synthesis of oxaspiro[4.5]decan-1-one scaffolds

    B. V. Subba Reddy, S. Gopal Reddy, M. Ramana Reddy, M. Pal Bhadra and A. V. S. Sarma, Org. Biomol. Chem., 2014, 12, 7257
    DOI: 10.1039/C4OB01188K

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