Issue 32, 2013
From the journal:

Organic & Biomolecular Chemistry

Enantioselective conjugate addition of 3-fluoro-oxindoles to vinyl sulfone: an organocatalytic access to chiral 3-fluoro-3-substituted oxindoles†

Xiaowei Doua  and  Yixin Lu*a  

* Corresponding authors

a Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Singapore 117543, Republic of Singapore
E-mail: chmlyx@nus.edu.sg

Abstract

An organocatalytic conjugate addition of prochiral 3-fluorinated oxindoles to vinyl sulfones was described for the first time. In the presence of bifunctional tertiary amine–thiourea catalysts, 3-fluoro-3-substituted oxindole adducts were obtained in excellent yields and with high enantiomeric excesses.

Graphical abstract: Enantioselective conjugate addition of 3-fluoro-oxindoles to vinyl sulfone: an organocatalytic access to chiral 3-fluoro-3-substituted oxindoles

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Article information

DOI
https://doi.org/10.1039/C3OB41267A
Article type
Communication
Submitted
19 Jun 2013
Accepted
27 Jun 2013
First published
27 Jun 2013

Org. Biomol. Chem., 2013,11, 5217-5221

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Enantioselective conjugate addition of 3-fluoro-oxindoles to vinyl sulfone: an organocatalytic access to chiral 3-fluoro-3-substituted oxindoles

X. Dou and Y. Lu, Org. Biomol. Chem., 2013, 11, 5217 DOI: 10.1039/C3OB41267A

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