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Mechanistic Investigation of the Asymmetric Addition of Trimethylsilyl Cyanide to Aldehydes Catalysed by Dinuclear Chiral (Salen)titanium Complexes
Author(s) -
Belokon’ Yuri N.,
Green Brendan,
Ikonnikov Nicolai S.,
Larichev Vladimir S.,
Lokshin Boris V.,
Moscalenko Margarita A.,
North Michael,
Orizu Charles,
Peregudov Alexander S.,
Timofeeva Galina I.
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200007)2000:14<2655::aid-ejoc2655>3.0.co;2-o
Subject(s) - trimethylsilyl cyanide , chemistry , trimethylsilyl , catalysis , cyanide , catalytic cycle , adduct , titanium , asymmetric induction , enantioselective synthesis , organic chemistry , cyanohydrin , combinatorial chemistry
Titanium complexes 1 derived from chiral salen ligands are highly active precatalysts for the asymmetric addition of trimethylsilyl cyanide to aldehydes and ketones. Based on spectroscopic studies and the identification of adducts between complexes 1 and carbonyl compounds or trimethylsilyl cyanide, a catalytic cycle which explains the origin of the asymmetric induction is proposed. Kinetics studies have been carried out, the results of which are consistent with the proposed catalytic cycle.