Issue 19, 2013

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

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

Supplementary files

Article information

Article type
Paper
Submitted
28 Feb 2013
Accepted
02 Apr 2013
First published
15 Apr 2013

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

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

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