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Synlett 2013; 24(18): 2446-2450
DOI: 10.1055/s-0033-1340046
DOI: 10.1055/s-0033-1340046
letter
Control of Hetero-Diels–Alder Stereoselectivity through Solvent Polarity and Brønsted or Lewis Acid Catalysis; Theory and Experiment
Further Information
Publication History
Received: 23 September 2013
Accepted after revision: 01 October 2013
Publication Date:
18 October 2013 (online)
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.
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