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Synthesis 2014; 46(14): 1917-1923
DOI: 10.1055/s-0033-1338638
DOI: 10.1055/s-0033-1338638
special topic
An Unexpected Inversion of Enantioselectivity in a Copper-Catalyzed Intramolecular Desymmetric Aryl C–N Coupling Reaction
Further Information
Publication History
Received: 20 February 2014
Accepted: 15 April 2014
Publication Date:
09 May 2014 (online)
Abstract
Enantioselective formation of indolines was achieved through desymmetrization of α,α-bis(2-iodobenzyl)glycines under the catalysis of copper(I) iodide and (2S,3aS,7aS)-octahydro-1H-indole-2-carboxylic acid. An unexpected inversion of enantioselectivity was observed when achiral additives such as 4-(N,N-dimethylamino)pyridine were added which work together with the ligand. The configuration-reversed products were obtained in moderate yields as well as moderate ee values.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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For reviews on copper-catalyzed carbon–heteroatom bond formation, see:
For selected examples, see:
For some important reviews on asymmetric desymmetrization, see:
For selected examples, see: