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Asymmetric aldol reaction of enol trichloroacetate catalyzed by ( S,S )‐(EBTHI)TiCl(OMe)
Author(s) -
Yanagisawa Akira,
Asakawa Kenichi,
Yamamoto Hisashi
Publication year - 2000
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(2000)12:5/6<421::aid-chir22>3.0.co;2-t
Subject(s) - chemistry , aldol reaction , enol , cyclohexanone , adduct , catalysis , methoxide , titanium , medicinal chemistry , organic chemistry
( S,S )‐Ethylenebis(tetrahydroindenyl)titanium chloride methoxide, ( S,S )‐(EBTHI)TiCl(OMe) ( 3 ) was synthesized from the corresponding titanium dichloride. The asymmetric aldol reaction of enol trichloroacetate of cyclohexanone 1 with aromatic aldehydes was studied in the presence of a catalytic amount of the chiral titanium complex 3 , with the result that the optically active syn aldol adduct 2 was preferentially obtained with up to 91% ee. Chirality 12:421–424, 2000. © 2000 Wiley‐Liss, Inc.