Parallel kinetic resolution of aziridines via chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening.
Chem Sci
; 14(43): 12152-12159, 2023 Nov 08.
Article
em En
| MEDLINE
| ID: mdl-37969581
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.
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MEDLINE
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En
Ano de publicação:
2023
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Article