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Catalytic Enantioselective Alkynylation of Trifluoromethyl Ketones: Pronounced Metal Fluoride Effects and Implications of Zinc‐to‐Titanium Transmetallation
Author(s) -
Zhang GuangWu,
Meng Wei,
Ma Hai,
Nie Jing,
Zhang WenQin,
Ma JunAn
Publication year - 2011
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.201007341
Subject(s) - transmetalation , enantioselective synthesis , trifluoromethyl , chemistry , catalysis , yield (engineering) , titanium , alkynylation , zinc , reactivity (psychology) , organic chemistry , enantiomer , fluoride , inorganic chemistry , materials science , metallurgy , medicine , alkyl , alternative medicine , pathology
Lost in transmetalation : The titanium(IV)‐catalyzed title reaction, utilizing chiral cinchona alkaloids as ligands ( L1 and L2 ), was developed for the synthesis of both enantiomers of trifluoromethylated propargylic tertiary alcohols in high yield and enantioselectivity. Small amounts of BaF 2 were found to be essential for maintaining high levels of reactivity and enantioselectivity.