Enantioselective organocatalytic anti-Mannich-type reaction of N-unprotected 3-substituted 2-oxindoles with aromatic N-Ts-aldimines

Liang Cheng; Li Liu; Han Jia; Dong Wang; Yong-Jun Chen

doi:10.1021/jo9006688

Enantioselective organocatalytic anti-Mannich-type reaction of N-unprotected 3-substituted 2-oxindoles with aromatic N-Ts-aldimines

J Org Chem. 2009 Jun 19;74(12):4650-3. doi: 10.1021/jo9006688.

Authors

Liang Cheng¹, Li Liu, Han Jia, Dong Wang, Yong-Jun Chen

Affiliation

¹ Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.

PMID: 19518155
DOI: 10.1021/jo9006688

Abstract

The modified cinchona alkaloid-catalyzed direct Mannich-type reaction of N-unprotected 2-oxindoles with N-Ts-imine was developed to afford anti-3,3-disubstituted 2-oxindoles with vicinal chiral quaternary and tertiary carbon centers in yields up to 90% with excellent diastereoselectivities (anti/syn up to 95:5) and good enantioselectivies (up to 89% ee). A transition model for the anti-diastereo- and enantioselectivity of the reaction was proposed.