Journal
CHEMICAL SCIENCE
Volume 6, Issue 7, Pages 4242-4246Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5sc01052g
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Funding
- ICIQ Foundation
- MINECO [CTQ2013-45938-P, SEV-2013-0319]
- CMIRA [006402-01]
- CELLEX Foundation
- ICREA Funding Source: Custom
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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 beta-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.
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