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Design and synthesis of chiral and regenerable [2.2]paracyclophane-based NAD(P)H models and application in biomimetic reduction of flavonoids.

ABSTRACT: With the rapid development of biomimetic asymmetric reduction, the demand for efficient chiral and regenerable NAD(P)H models is growing rapidly. Herein, a new class of [2.2]paracyclophane-based chiral and regenerable NAD(P)H models (CYNAMs) was designed and synthesized. The first enantioselective biomimetic reduction of tetrasubstituted alkene flavonoids has been successfully realized through enzyme-like cooperative bifunctional activation, giving chiral flavanones with up to 99% yield and 99% ee.

SUBMITTER: Zhu ZH

PROVIDER: S-EPMC8162316 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature

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Design and synthesis of chiral and regenerable [2.2]paracyclophane-based NAD(P)H models and application in biomimetic reduction of flavonoids.

Zhu Zhou-Hao ZH Ding Yi-Xuan YX Wu Bo B Zhou Yong-Gui YG

Chemical science 20200910 37

With the rapid development of biomimetic asymmetric reduction, the demand for efficient chiral and regenerable NAD(P)H models is growing rapidly. Herein, a new class of [2.2]paracyclophane-based chiral and regenerable NAD(P)H models (CYNAMs) was designed and synthesized. The first enantioselective biomimetic reduction of tetrasubstituted alkene flavonoids has been successfully realized through enzyme-like cooperative bifunctional activation, giving chiral flavanones with up to 99% yield and 99% ...[more]

PMID: 34094287

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