143237-03-0Relevant academic research and scientific papers
The design of diastereoselective Mukaiyama-Michael reaction of ketene silyl acetal
Otera, Junzo,Fujita, Yukihiro,Fukuzumi, Shunichi
, p. 9409 - 9418 (1996)
The highly diastereoselective Mukaiyama-Michael reaction has been designed. Suppression of an electron-transfer process is crucial for this purpose and the following conditions should be satisfied. (1) TiCl4 is employed as a Lewis acid. (2) Ketene silyl acetals have bulky siloxy and/or alkoxy group(s). (3) α-Enones have a bulky acyl group. The excellent syn- selectivity up to a 99:1 ratio is attained under these conditions. The selectivity is reversed to the anti-preference upon decreasing the size of the alkoxy group.
How Can High Diastereoselectivity Be Attained in the Michael Addition of Ketene Silyl Acetals?
Otera, Junzo,Fujita, Yukihiro,Sato, Tsuneo,Nozaki, Hitosi,Fukuzumi, Shunichi,Fujita, Morifumi
, p. 5054 - 5055 (2007/10/02)
Criteria for attaining high diastereoselectivity in the title reaction are elucidated in terms of suppressing an electron-transfer process.
