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Issue 17, 2017
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6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis

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Abstract

The catalytic enantioselective 6-exo-trig Michael addition-lactonization of enone-acid substrates to form cis-chromenones with high diastereo- and enantiocontrol was developed using the commercially available isothiourea tetramisole. An acidic workup proved necessary to minimize product epimerization and maximize product er, providing cis-chromenones in excellent yield, and with excellent diastereo- and enantioselectivity.

Graphical abstract: 6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis

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Supplementary files

Article information


Submitted
23 Dec 2016
Accepted
18 Jan 2017
First published
19 Jan 2017

This article is Open Access

Chem. Commun., 2017,53, 2555-2558
Article type
Communication

6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis

R. M. Neyyappadath, D. B. Cordes, A. M. Z. Slawin and A. D. Smith, Chem. Commun., 2017, 53, 2555
DOI: 10.1039/C6CC10178J

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