Synthesis of β- and β, β-substituted Morita-Baylis-Hilmann Adducts Using a Two-Step Protocol

Journal article

Authors/Editors

Ravi, Samikannu

Research Areas

ENGINEERING AND TECHNOLOGY (Frascati classification)

Publication Details

Subtitle: Synthesis of β- and β, β-substituted Morita-Baylis-Hilmann Adducts Using a Two-Step Protocol

Author list: Ravi, Samikannu

Publisher: NRC Research Press (Canadian Science Publishing)

Publication year: 2012

Journal: Canadian Journal of Chemistry (0008-4042)

Volume number: 90

Issue number: 5

Start page: 450

End page: 463

Number of pages: 14

ISSN: 0008-4042

eISSN: 1480-3291

URL: https://www.nrcresearchpress.com/doi/abs/10.1139/v2012-017#.XUppJPIzZdg

Languages: English-United States (EN-US)

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Abstract

The synthesis of a large number of β- and β,β-substituted keto esters was successful by the use of the Knoevenagel condensation reaction. The stereoselectivity of these reactions was improved by alteration of various substituent groups. Although there were few examples of complete Z selectivity, the use of tert-butyl acetoacetate with either aromatic or aliphatic aldehydes afforded Z selectivity. The selective reductions of these substituted keto esters was successfully achieved by using a combination of NaBH4 and CeCl3·7H2O or Yb(OTf)3, which allowed a facile synthesis of a large number of stereochemically pure substituted Morita–Baylis–Hillman adducts, including β,β-substituted adducts.

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