4.4 Article

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

Journal

SYNLETT
Volume 25, Issue 5, Pages 713-717

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0033-1340669

Keywords

acetals; desymmetrization; Michael addition; stereoselective synthesis; cascade catalysis

Funding

  1. NIGMS [GM72586]

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

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