Issue 5, 2010

Highly enantioselective synthesis of 1,3-bis(hydroxymethyl)-2-oxindoles from unprotected oxindoles and formalin using a chiral NdIII complex

Abstract

Highly enantioselective synthesis of 1,3-bis(hydroxymethyl)-2-oxindoles was established through chiral NdIII-N,N′-dioxide in up to 93% yield and >99% ee under mild conditions. The key features of this approach include using cheap and readily available formalin as a hydroxymethylation C1 unit and unprotected 3-substituted-2-oxindoles as nucleophiles directly. The initial C-aldol product from 3-substituted-2-oxindole was converted to the corresponding 1,3-bis(hydroxymethyl)-2-oxindole derivative immediately under the reaction conditions. Moreover, the catalyst was water-tolerant, and ligand and Nd(OTf)3 could be easily recovered and reused with no loss in catalytic activity and enantioselectivity. The synthetic utility of this methodology was accomplished with the synthesis of key intermediates of physostigmine and coerulescine.

Graphical abstract: Highly enantioselective synthesis of 1,3-bis(hydroxymethyl)-2-oxindoles from unprotected oxindoles and formalin using a chiral NdIII complex

Supplementary files

Article information

Article type
Edge Article
Submitted
23 Jul 2010
Accepted
30 Aug 2010
First published
21 Sep 2010

Chem. Sci., 2010,1, 590-595

Highly enantioselective synthesis of 1,3-bis(hydroxymethyl)-2-oxindoles from unprotected oxindoles and formalin using a chiral NdIII complex

K. Shen, X. Liu, W. Wang, G. Wang, W. Cao, W. Li, X. Hu, L. Lin and X. Feng, Chem. Sci., 2010, 1, 590 DOI: 10.1039/C0SC00385A

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