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Synthesis 2016; 48(14): 2271-2279
DOI: 10.1055/s-0035-1561634
DOI: 10.1055/s-0035-1561634
paper
Synthesis of Chiral Tetrahydroisoquinoline and C 2-Symmetric Bistetrahydroisoquinoline Ligands and Their Application in the Enantioselective Henry Reaction
Further Information
Publication History
Received: 16 November 2015
Accepted after revision: 08 April 2016
Publication Date:
01 June 2016 (online)
Abstract
Application of chiral tetrahydroisoquinoline and bistetrahydroisoquinoline scaffolds in asymmetric reactions is limited by the inefficient synthesis of their chiral structural variants. We have conveniently synthesized 24 such variants and applied them as ligands in the enantioselective Henry reaction. The conformational rigidity of these ligands and the size of the coordination sphere control the enantioselectivity of the products. The conformationally rigid chiral tetrahydroisoquinoline THIQ–Cu(OAc)2·H2O complex successfully catalyzed the enantioselective Henry reaction between various aldehydes and nitromethane and gives the β-nitro alcohol adducts in up to 96% yield and 80% ee.
Key words
tetrahydroisoquinoline - C 2-symmetric ligand - bistetrahydroisoquinoline - Henry reaction - asymmetric catalysisSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561634.
- Supporting Information
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