Premium
Inside Cover: Lewis Acid Activated Synthesis of Highly Substituted Cyclopentanes by the N‐Heterocyclic Carbene Catalyzed Addition of Homoenolate Equivalents to Unsaturated Ketoesters (Angew. Chem. Int. Ed. 7/2011)
Author(s) -
Cohen Daniel T.,
CardinalDavid Benoit,
Scheidt Karl A.
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201007985
Subject(s) - carbene , cyclopentanes , stereocenter , catalysis , lewis acids and bases , yield (engineering) , enantioselective synthesis , chemistry , medicinal chemistry , stereochemistry , organic chemistry , materials science , metallurgy
A highly diastereo‐ and enantioselective N‐heterocyclic carbene catalyzed/titanium(IV)‐mediated homoenolate addition to β,γ‐unsaturated α‐ketoesters to assemble cyclopentanols with four contiguous stereogenic centers is described by Scheidt and co‐workers in their Communication on page 1678 ff. The Lewis acid is essential for the reaction and a wide range of β,γ‐unsaturated α‐ketoesters and enals are tolerated, with the products obtained in 52–85% yield and up to 99% ee.