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Issue 2, 2017
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Catalytic asymmetric aldol addition reactions of 3-fluoro-indolinone derived enolates

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Abstract

Reported herein is a Cu(I)/bisoxazoline ligand-catalyzed aldol reaction of unprotected tertiary enolates generated in situ from 3-(1,1-dihydroxy-2,2,2-trifluoroethyl)-substituted derivatives of 3-fluoro-2-oxindoles. A range of α-fluoro-β-aryl/hetaryl/alkyl-β-hydroxy-indolin-2-ones containing C–F quaternary stereogenic centers of high pharmaceutical importance were furnished in good yields and satisfactory diastereo- and enantioselectivities. The reactions were conducted under operationally convenient conditions and displayed wide substrate/functional group generality including unprotected N–H on the tertiary enolates, and aromatic, hetero-aromatic and aliphatic aldehydes.

Graphical abstract: Catalytic asymmetric aldol addition reactions of 3-fluoro-indolinone derived enolates

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Article information


Submitted
10 Nov 2016
Accepted
25 Nov 2016
First published
25 Nov 2016

Org. Biomol. Chem., 2017,15, 311-315
Article type
Communication

Catalytic asymmetric aldol addition reactions of 3-fluoro-indolinone derived enolates

L. Zhang, W. Zhang, H. Mei, J. Han, V. A. Soloshonok and Y. Pan, Org. Biomol. Chem., 2017, 15, 311
DOI: 10.1039/C6OB02454H

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