Mukaiyama Aldol-Prins Cyclizations with Ketones

Brian Patterson; Scott D. Rychnovsky

doi:10.1055/s-2004-815424

LETTER

Mukaiyama Aldol-Prins Cyclizations with Ketones

Brian Patterson, Scott D. Rychnovsky*
Department of Chemistry, University of California, 516 Rowland Hall, Irvine, CA 92697-2025, USA
Fax: +1(949)8569567; e-Mail: srychnov@uci.edu;

Abstract

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Abstract

The Mukaiyama aldol-Prins (MAP) cyclization with ketones is described. These reactions produce substituted tetrahydropyrans efficiently and in some cases with high stereoselectivity. Cyclizations with E- and Z-alkenes are shown to be stereospecific. These studies extend the scope of the MAP cyclizations promoted by titanium tetrabromide.

Key words

tandem reactions - annulations - aldol reaction - stereoselective - carbocations

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Referenzen

References

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The configurations of the stereocenters in 8 and 9 were determined by analysis of the ¹H NMR coupling constants and of the NOESY spectra.