Synthesis of beta- and beta,beta-substituted Morita-Baylis-Hillman adducts using a two-step protocol

Journal article

Authors / Editors

Ratshonka, Same

Research Areas

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Publication Details

Author list: Magee DI, Ratshonka S, McConaghy J, Hood M

Publisher: NRC Research Press (Canadian Science Publishing)

Place: OTTAWA

Publication year: 2012

Journal: Canadian Journal of Chemistry (0008-4042)

Journal acronym: CAN J CHEM

Volume number: 90

Issue number: 5

Start page: 450

End page: 463

Number of pages: 14

ISSN: 0008-4042

eISSN: 1480-3291

Languages: English-Great Britain (EN-GB)

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Abstract

The synthesis of a large number of beta- and beta,beta-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 center dot 7H(2)O or Yb(OTf)(3), which allowed a facile synthesis of a large number of stereochemically pure substituted Morita-Baylis-Hillman adducts, including b, b-substituted adducts.

Keywords

beta,beta-substituted, Knoevenagel, Morita-Baylis-Hillman, Reduction

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