Synlett 2014; 25(5): 713-717
DOI: 10.1055/s-0033-1340669
letter
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Synthesis of Dioxolanes and Oxazolidines via a Desymmetrization Acetalization/Michael Cascade

David M. Rubush
Colorado State University, Department of Chemistry, Fort Collins, CO 80523, USA   Fax: +1(970)4911801   eMail: rovis@lamar.colostate.edu
,
Tomislav Rovis*
Colorado State University, Department of Chemistry, Fort Collins, CO 80523, USA   Fax: +1(970)4911801   eMail: rovis@lamar.colostate.edu
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Publikationsverlauf

Received: 04. Oktober 2013

Accepted after revision: 02. Januar 2014

Publikationsdatum:
10. Februar 2014 (online)


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Abstract

The desymmetrization of p-quinols using a Brønsted acid catalyzed acetalization/Michael cascade was achieved in high yields and diastereoselectivities for aldehydes and imines. Use of a chiral Brønsted acid allowed for the synthesis of 1,3-dioxolane and 1,3-oxazolidine products in modest enantioselectivity.

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