The design of diastereoselective Mukaiyama-Michael reaction of ketene silyl acetal

Junzo Otera; Yukihiro Fujita; Shunichi Fukuzumi

doi:10.1016/0040-4020(96)00478-4

The design of diastereoselective Mukaiyama-Michael reaction of ketene silyl acetal

Junzo Otera, Yukihiro Fujita, Shunichi Fukuzumi

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	9409-9418
Number of pages	10
Journal	Tetrahedron
Volume	52
Issue number	28
DOIs	https://doi.org/10.1016/0040-4020(96)00478-4
State	Published - 8 Jul 1996

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abstract = "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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The design of diastereoselective Mukaiyama-Michael reaction of ketene silyl acetal

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