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Synlett 2013; 24(18): 2446-2450
DOI: 10.1055/s-0033-1340046
letter
© Georg Thieme Verlag Stuttgart · New York

Control of Hetero-Diels–Alder Stereoselectivity through Solvent Polarity and Brønsted or Lewis Acid Catalysis; Theory and Experiment

Olivier Loiseleur*
a  Syngenta Crop Protection AG, Research Chemistry, 4332 Stein, Switzerland   Email: olivier.loiseleur@syngenta.com
,
Jérôme Cassayre
a  Syngenta Crop Protection AG, Research Chemistry, 4332 Stein, Switzerland   Email: olivier.loiseleur@syngenta.com
,
Dominique Leca
a  Syngenta Crop Protection AG, Research Chemistry, 4332 Stein, Switzerland   Email: olivier.loiseleur@syngenta.com
,
Francesca Gaggini
a  Syngenta Crop Protection AG, Research Chemistry, 4332 Stein, Switzerland   Email: olivier.loiseleur@syngenta.com
,
Susan N. Pieniazek
b  Department of Chemistry and Biochemistry, University of California Los Angeles, CA 90095-1569, USA
,
Jennifer A. R. Luft
b  Department of Chemistry and Biochemistry, University of California Los Angeles, CA 90095-1569, USA
,
Kendall N. Houk*
b  Department of Chemistry and Biochemistry, University of California Los Angeles, CA 90095-1569, USA
› Author Affiliations
Further Information

Publication History

Received: 23 September 2013

Accepted after revision: 01 October 2013

Publication Date:
18 October 2013 (online)

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Abstract

The stereoselectivity of cycloadditions involving 3-methyleneoxindole and 2-azadienes can be controlled by solvent polarity and by Lewis or Brønsted acid catalysis. The improvements in selectivity are advantageous for the synthesis of spiroquinazoline alkaloids such as alantrypinone and lapatin B.

Key words

spiroquinazoline alkaloids - stereoselectivity - Lewis acid catalysis - hetero-Diels–Alder - natural products
 

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