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Org Lett. 2012 Jan 6;14(1):58-61. doi: 10.1021/ol202829u. Epub 2011 Nov 30.

The Prins reaction using ketones: rationalization and application toward the synthesis of the portentol skeleton.

Author information

1
Université de Rennes 1, UMR 6226, Sciences Chimiques de Rennes, Equipe PNSCM, UFR des Sciences Biologiques et Pharmaceutiques, 2 avenue du Prof Léon Bernard, F-35043 Rennes Cedex, France.

Abstract

We report a TMSI-promoted Prins cyclization reaction with ketones as carbonyl partners to prepare polysubstituted chiral spirotetrahydropyrans. In the presence of racemic 2-methylcyclohexanone a dynamic kinetic resolution occurred affording one stereoisomer. The observed enantiospecificity has been rationalized by DFT calculation.

PMID:
22128826
DOI:
10.1021/ol202829u
[Indexed for MEDLINE]

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