Issue 19, 2013
From the journal:

Organic & Biomolecular Chemistry

NHC-mediated enantioselective formal [4 + 2] cycloadditions of alkylarylketenes and β,γ-unsaturated α-ketocarboxylic esters and amides†

Stuart M. Leckie,a   T. Bruce Brown,b   David Pryde,c   Tomas Lebl,a   Alexandra M. Z. Slawina  and  Andrew D. Smith*a  

* Corresponding authors

a EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, UK
E-mail: ads10@st-andrews.ac.uk
Tel: +44 (0)1334 463 89

b Pfizer Global Research and Development, 388 Ramsgate Road, Sandwich, Kent, UK

c Pfizer Neusentis, The Portway Building, Granta Park, Great Abington, Cambridge, UK

Abstract

Chiral N-heterocyclic carbenes (NHCs) promote the asymmetric formal [4 + 2] cycloaddition of alkylarylketenes with β,γ-unsaturated α-ketocarboxylic esters and amides. Divergent diastereoselectivity is observed in this process, with γ-aryl-β,γ-unsaturated α-ketocarboxylic esters and amides giving preferentially syn-dihydropyranones (up to 68 : 32 dr syn : anti, up to 98% ee), while γ-alkyl-derivatives generate anti-dihydropyranones (up to 18 : 82 dr syn : anti, up to 75% ee).

Graphical abstract: NHC-mediated enantioselective formal [4 + 2] cycloadditions of alkylarylketenes and β,γ-unsaturated α-ketocarboxylic esters and amides

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C3OB40424B
Article type
Paper
Submitted
28 Feb 2013
Accepted
02 Apr 2013
First published
15 Apr 2013

Org. Biomol. Chem., 2013,11, 3230-3246

Permissions

Request permissions

NHC-mediated enantioselective formal [4 + 2] cycloadditions of alkylarylketenes and β,γ-unsaturated α-ketocarboxylic esters and amides

S. M. Leckie, T. B. Brown, D. Pryde, T. Lebl, A. M. Z. Slawin and A. D. Smith, Org. Biomol. Chem., 2013, 11, 3230 DOI: 10.1039/C3OB40424B

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements