Isothiourea-catalyzed enantioselective Michael addition of malonates to α,β-unsaturated aryl esters

Jiufeng Wu, Claire Mary Young, Amy A. Watts, Alexandra Martha Zoya Slawin, Greg Boyce*, Michael Buehl*, Andrew David Smith*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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Abstract

An enantioselective Michael addition of malonates to α,β-unsaturated para-nitrophenyl esters was achieved using the Lewis basic isothiourea HyperBTM, giving excellent levels of product enantioselectivity (up to >99:1 enantiomeric ratio) in good yields and with complete regioselectivity (>20:1 regioselectivity ratio) in the presence of alternative (phenyl ketone and ethyl ester) Michael acceptors. Density functional theory calculations indicate that N-acylation is rate-limiting. This constitutes a rare example of a highly enantioselective addition of simple, readily available malonates to α,β-unsaturated esters.
Original languageEnglish
Pages (from-to)4040-4045
Number of pages6
JournalOrganic Letters
Volume24
Issue number22
Early online date2 Jun 2022
DOIs
Publication statusPublished - 10 Jun 2022

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