Issue 17, 2017
From the journal:

Chemical Communications

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

Rifahath M. Neyyappadath,a   David B. Cordes, ORCID logo a   Alexandra M. Z. Slawina  and  Andrew D. Smith ORCID logo *a  

* Corresponding authors

a EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, UK
E-mail: ads10@st-andrews.ac.uk

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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Article information

DOI
https://doi.org/10.1039/C6CC10178J
Article type
Communication
Submitted
23 dec 2016
Accepted
18 jan 2017
First published
19 jan 2017
This article is Open Access
Creative Commons BY license

Chem. Commun., 2017,53, 2555-2558

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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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