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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

✍ Scribed by Rudhramyna Gnaneshwar; Prakash P. Wadgaonkar; Swaminathan Sivaram

Book ID: 104254125
Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 81 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)01511-9

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✦ Synopsis

The Michael addition of a b,b-dimethyl substituted silyl ketene acetal [Me 2 C C(OMe)OSiMe 3 ] to a,b-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.

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