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Org Lett. 2012 Dec 21;14(24):6130-3. doi: 10.1021/ol302669q. Epub 2012 Dec 13.

Regioselective prins cyclization of allenylsilanes. Stereoselective formation of multisubstituted heterocyclic compounds.

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1
Graduate School of Science, Osaka City University, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan.

Abstract

The Prins cyclization of hydroxy or amino group-containing allenylsilanes with carbonyl compounds occurred at the allenic terminus in a regio- and stereoselective manner to give the di- or trisubstituted tetrahydrofurans, tetrahydropyrans, and pyrrolidines. During the reaction, the allenic axial chirality of the starting material was efficiently transferred to the newly formed carbon chiral centers of the product.

PMID:
23237587
DOI:
10.1021/ol302669q
[Indexed for MEDLINE]
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