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Stereoselective Biginelli-like reaction catalyzed by a chiral phosphoric acid bearing two hydroxy groups.

ABSTRACT: To develop new efficient stereoselective catalysts for Biginelli-like reactions, a chiral phosphoric acid bearing two hydroxy groups derived from ?-tartaric acid was successfully synthesized via highly regioselective transformations of enantiopure 1,1,4,4-tetraphenylbutanetetraol. The obtained catalyst effectively catalyzed Biginelli-like reactions with moderate to good enantioselectivities. Control experiments indicated that the presence of the two hydroxy groups were indispensable for achieving a high enantioselectivity.

SUBMITTER: Hu X

PROVIDER: S-EPMC7404148 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Stereoselective Biginelli-like reaction catalyzed by a chiral phosphoric acid bearing two hydroxy groups.

Hu Xiaoyun X Hu Xiaoyun X Guo Jianxin J Wang Cui C Zhang Rui R Borovkov Victor V

Beilstein journal of organic chemistry 20200731

To develop new efficient stereoselective catalysts for Biginelli-like reactions, a chiral phosphoric acid bearing two hydroxy groups derived from ʟ-tartaric acid was successfully synthesized via highly regioselective transformations of enantiopure 1,1,4,4-tetraphenylbutanetetraol. The obtained catalyst effectively catalyzed Biginelli-like reactions with moderate to good enantioselectivities. Control experiments indicated that the presence of the two hydroxy groups were indispensable for achievin ...[more]

PMID: 32802205

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