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Catalytic Enantioselective Desymmetrization of Prochiral Triacylamines via Pseudopeptidic Guanidine-Guanidinium Catalysis. | LitMetric

Catalytic Enantioselective Desymmetrization of Prochiral Triacylamines via Pseudopeptidic Guanidine-Guanidinium Catalysis.

Org Lett

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000, China.

Published: September 2022

AI Article Synopsis

  • * The catalytic process relies on chiral pseudopeptidic guanidine-guanidinium salts, which have weakly coordinating anions, to achieve enantioselectivity.
  • * The advanced methodology generates valuable chiral imide-esters featuring a 1,5-dicarbonyl structure and has practical applications in synthesizing two drugs that are analogues of GABA: ()-Baclofen·HCl and ()-Pregabalin.

Article Abstract

Triacylamines with symmetry have been explored in asymmetric organocatalysis, leading to the development of a novel catalytic enantioselective desymmetrization of prochiral triacylamines by methanolysis under the catalysis of chiral pseudopeptidic guanidine-guanidinium salt having a weakly coordinating anion. This organocatalytic methodology provides an effective approach to the synthetically useful chiral imide-esters with a 1,5-dicarbonyl moiety, and its synthetic potential has been manifested in the asymmetric synthesis of two GABA analogue drugs, ()-Baclofen·HCl and ()-Pregabalin.

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Source
http://dx.doi.org/10.1021/acs.orglett.2c02785DOI Listing

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