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Acylzirconocene Chloride as an “Unmasked” Acyl Anion: Enantioselective 1,2‐Addition to α , β ‐Unsaturated Ketone Derivatives
Author(s) -
Hanzawa Yuji,
Tabuchi Nobuhito,
Saito Kosuke,
Noguchi Satoshi,
Taguchi Takeo
Publication year - 1999
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/(sici)1521-3773(19990816)38:16<2395::aid-anie2395>3.0.co;2-w
Subject(s) - enantioselective synthesis , chemistry , ketone , nucleophile , medicinal chemistry , denticity , yield (engineering) , ligand (biochemistry) , chloride , nucleophilic addition , catalysis , organic chemistry , receptor , crystal structure , biochemistry , materials science , metallurgy
The chiral monodentate phosphane ligand ( R )‐MOP facilitated the first enantioselective nucleophilic 1,2‐addition of an “unmasked” acyl anion to a carbonyl group in the Pd II ‐catalyzed reaction of α , β ‐unsaturated ketones with acylzirconocene chlorides [Eq. (1), 66 % ee , 88 % yield; ( R )‐MOP=( R )‐2‐(diphenylphosphanyl)‐2′‐methoxy‐1,1′‐binaphthyl].