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Parallel kinetic resolution of aziridines via chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening.

ABSTRACT: We report a chiral phosphoric acid catalyzed apparent hydrolytic ring-opening reaction of racemic aziridines in a regiodivergent parallel kinetic resolution manner. Harnessing the acyloxy-assisted strategy, the highly stereocontrolled nucleophilic ring-opening of aziridines with water is achieved. Different kinds of aziridines are applicable in the process, giving a variety of enantioenriched aromatic or aliphatic amino alcohols with up to 99% yields and up to >99.5 : 0.5 enantiomeric ratio. Preliminary mechanistic study as well as product elaborations were inducted as well.

SUBMITTER: Liu J 

PROVIDER: S-EPMC10631200 | biostudies-literature | 2023 Nov

REPOSITORIES: biostudies-literature

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Parallel kinetic resolution of aziridines <i>via</i> chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening.

Liu Juan J   Du Yi-Ying YY   He Yu-Shi YS   Liang Yan Y   Liu Shang-Zhong SZ   Li Yi-Yi YY   Cao Yi-Ming YM  

Chemical science 20231012 43

We report a chiral phosphoric acid catalyzed apparent hydrolytic ring-opening reaction of racemic aziridines in a regiodivergent parallel kinetic resolution manner. Harnessing the acyloxy-assisted strategy, the highly stereocontrolled nucleophilic ring-opening of aziridines with water is achieved. Different kinds of aziridines are applicable in the process, giving a variety of enantioenriched aromatic or aliphatic amino alcohols with up to 99% yields and up to >99.5 : 0.5 enantiomeric ratio. Pre  ...[more]

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