Issue 7, 2015

Diastereodivergent organocatalysis for the asymmetric synthesis of chiral annulated furans

Abstract

Disclosed herein is a stereoselective method for the synthesis of 2,3-furan fused carbocycles bearing adjacent quaternary and tertiary carbon stereocenters. The chemistry is based on an asymmetric addition of β-ketoesters to 2-(1-alkynyl)-2-alkene-1-ones catalysed by natural cinchona alkaloids followed by a silver-catalysed intramolecular cycloisomerisation. By exploiting the distinct catalysis modes of quinine, which can act either as a general base or, upon opportune modifications, as a phase transfer catalyst, a complete switch of the enforced sense of diastereoinduction is achieved. The stereodivergent systems enable access to the full matrix of all possible stereoisomeric products.

Graphical abstract: Diastereodivergent organocatalysis for the asymmetric synthesis of chiral annulated furans

Supplementary files

Article information

Article type
Edge Article
Submitted
23 Mar 2015
Accepted
25 Apr 2015
First published
27 Apr 2015
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2015,6, 4242-4246

Author version available

Diastereodivergent organocatalysis for the asymmetric synthesis of chiral annulated furans

C. Verrier and P. Melchiorre, Chem. Sci., 2015, 6, 4242 DOI: 10.1039/C5SC01052G

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