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

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.

SUBMITTER: Rubush DM 

PROVIDER: S-EPMC4422513 | biostudies-literature | 2014 Mar

REPOSITORIES: biostudies-literature

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

Rubush David M DM   Rovis Tomislav T  

Synlett : accounts and rapid communications in synthetic organic chemistry 20140301 5

The desymmetrization of <i>p</i>-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. ...[more]

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