354581-77-4Relevant academic research and scientific papers
Dimethylsilyl ketene acetal as a nucleophile in asymmetric Michael reaction: Enhanced enantioselectivity in oxazaborolidinone-catalyzed reaction
Harada, Toshiro,Adachi, Shinya,Wang, Xiaowei
, p. 4877 - 4879 (2004)
(Chemical Equation Presented) Dimethylsilanyl [Me2Si(H)] ketene S,O-acetal 6b is an effective nucleophile that retards the undesirable Si +-catalyzed racemic pathway in the oxazaborolidinone-catalyzed asymmetric Michael reaction. Thr
Enantioselective Lewis Acid-Catalyzed Mukaiyama-Michael Reactions of Acyclic Enones. Catalysis by allo-Threonine-Derived Oxazaborolidinones
Wang, Xiaowei,Adachi, Shinya,Iwai, Hiroyoshi,Takatsuki, Hiroshi,Fujita, Katsuhiro,Kubo, Mikako,Oku, Akira,Harada, Toshiro
, p. 10046 - 10057 (2007/10/03)
allo-Threonine-derived O-aroyl-B-phenyl-N-tosyl-1,3,2 -oxazaborolidin-5-ones 1g,n catalyze the asymmetric Mukaiyama-Michael reaction of acyclic enones with a trimethylsilyl ketene S,O-acetal in high enantioselectivity. A range of alkenyl methyl ketones is successfully employed as Michael acceptors affording ee values of 85-90% by using 10 mol % of the catalyst. The use of 2,6-diisopropylphenol and tert-butyl methyl ether as additives is found to be essential to achieve high enantioselectivity in these reactions. The effects of the additives are discussed in terms of the retardation of an Si+-catalyzed racemic pathway, which seriously deteriorates the enantioselectivity of asymmetric Mukaiyama-Michael reactions. A working model for asymmetric induction is proposed based on correlation between catalyst structures and enantioselectivities.
Asymmetric Mukaiyama-Michael Addition of Acyclic Enones Catalyzed by allo-Threonine-Derived B-Aryloxazaborolidinones
Harada, Toshiro,Iwai, Hiroyoshi,Takatsuki, Hiroshi,Fujita, Katsuhiro,Kubo, Mikako,Oku, Akira
, p. 2101 - 2103 (2007/10/03)
(Formula Presented) O-(2-Naphthoyl)-N-tosyl-L-allo-threonine-derived B-phenyloxazaborolidinone catalyzes the asymmetric Mukaiyama-Michael addition of simple acyclic enones to give adducts of 54-85% ee. 2,6-Diisopropylphenol as an additive is demonstrated
