Tetrahedron p. 9409 - 9418 (1996)
Update date:2022-09-26
Topics:
Otera, Junzo
Fujita, Yukihiro
Fukuzumi, Shunichi
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.
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