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Highly Diastereoselective Tandem Reduction–Allylation Reactions of 1,4‐Diketones with Zirconocene–Olefin Complexes
Author(s) -
Fujita Kazuya,
Shinokubo Hiroshi,
Oshima Koichiro
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200351480
Subject(s) - chemistry , stereocenter , alkene , olefin fiber , hydride , nucleophile , tandem , medicinal chemistry , stereochemistry , organic chemistry , catalysis , enantioselective synthesis , materials science , composite material , hydrogen
Terminal alkenes act as dual nucleophiles in a zirconocene‐mediated, highly 1,4‐diastereoselective, tandem reduction–allylation reaction of 1,4‐diketones. A zirconocene–alkene complex (in equilibrium with an allyl–zirconocene–hydride species) can deliver both hydride and an allyl group to a diketone, with control of the relative configuration of up to three new stereogenic centers (see scheme).