Premium
Highly Enantioselective Synthesis of γ‐Hydroxy‐α,β‐acetylenic Esters by Asymmetric Alkyne Addition to Aldehydes
Author(s) -
Gao Ge,
Wang Qin,
Yu XiaoQi,
Xie RuGang,
Pu Lin
Publication year - 2005
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.200500469
Subject(s) - enantioselective synthesis , alkyne , reagent , chemistry , hexamethylphosphoramide , ligand (biochemistry) , combinatorial chemistry , addition reaction , organic chemistry , catalysis , biochemistry , receptor
Alkynoates are added to aromatic and α,β‐unsaturated aldehydes in the synthesis of the title compounds in optically active form. This highly enantioselective and useful method is carried out under mild reaction conditions and employs the readily available chiral 1,1′‐bi‐2‐naphthol (binol) ligand and the metal reagents Et 2 Zn and [Ti(O i Pr) 4 ] (see scheme; HMPA=hexamethylphosphoramide).