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

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Wu_2022_OL_Isothiourea_catalyzed_CC.pdf (1.189Mb)
Date
10/06/2022
Author
Wu, Jiufeng
Young, Claire Mary
Watts, Amy A.
Slawin, Alexandra Martha Zoya
Boyce, Greg
Buehl, Michael
Smith, Andrew David
Keywords
QD Chemistry
DAS
MCC
Metadata
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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.
Citation
Wu , J , Young , C M , Watts , A A , Slawin , A M Z , Boyce , G , Buehl , M & Smith , A D 2022 , ' Isothiourea-catalyzed enantioselective Michael addition of malonates to α,β-unsaturated aryl esters ' , Organic Letters , vol. 24 , no. 22 , pp. 4040-4045 . https://doi.org/10.1021/acs.orglett.2c01486
Publication
Organic Letters
Status
Peer reviewed
DOI
https://doi.org/10.1021/acs.orglett.2c01486
ISSN
1523-7060
Type
Journal article
Rights
Copyright © 2022 The Authors. Open Access article Licensed under Creative Commons Attribution CC-BY 4.0.
Description
MB thanks EaStCHEM and the School of Chemistry for support.
Collections
  • University of St Andrews Research
URI
http://hdl.handle.net/10023/25486

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