The Mukaiyama–Michael addition of a β,β-dimethyl substituted silyl ketene acetal to α,β-unsaturated ketones using tetra-n-butylammonium bibenzoate as a nucleophilic catalyst

Gnaneshwar, Rudhramyna ; Wadgaonkar, Prakash P. ; Sivaram, Swaminathan (2003) The Mukaiyama–Michael addition of a β,β-dimethyl substituted silyl ketene acetal to α,β-unsaturated ketones using tetra-n-butylammonium bibenzoate as a nucleophilic catalyst Tetrahedron Letters, 44 (32). pp. 6047-6049. ISSN 0040-4039

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/S0040-4039(03)01511-9

Abstract

The Michael addition of a β,β-dimethyl substituted silyl ketene acetal [Me2C=C(OMe)OSiMe3] to α,β-unsaturated ketones, namely, 2-cyclopentenone, 2-cyclohexenone, 3-methyl-2-cyclohexenone, isophorone, methyl vinyl ketone and mesityl oxide occurs smoothly in the presence of the nucleophilic catalyst, tetra-n-butyl ammonium bibenzoate (TBABB) in THF giving the corresponding 1,4-adducts in excellent yields.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Mukaiyama-Michael Reactions; Conjugate Addition; 1,4-addition; δ-ketoester; O-silylated Ketene Acetal; α, β-unsaturated Ketones
ID Code:48566
Deposited On:14 Jul 2011 14:21
Last Modified:14 Jul 2011 14:21

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