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

About
Cited by
Related
Download options Please wait...

Supplementary files

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

Permissions

Request permissions

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements