Ni-Catalyzed asymmetric reduction of α-keto-β-lactams via DKR enabled by proton shuttling

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review

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Author(s)

  • Fangyuan Wang
  • Ting Wu
  • Long-Sheng Zheng
  • Gen-Qiang Chen
  • Xumu Zhang

Detail(s)

Original languageEnglish
Pages (from-to)15557-15560
Journal / PublicationChemical Communications
Volume56
Issue number99
Online published18 Nov 2020
Publication statusPublished - 25 Dec 2020
Externally publishedYes

Abstract

Chiral α-hydroxy-β-lactams are key fragments of many bioactive compounds and antibiotics, and the development of efficient synthetic methods for these compounds is of great value. The highly enantioselective dynamic kinetic resolution (DKR) of α-keto-β-lactams was realized via a novel proton shuttling strategy. A wide range of α-keto-β-lactams were reduced efficiently and enantioselectively by Ni-catalyzed asymmetric hydrogenation, providing the corresponding α-hydroxy-β-lactam derivatives with high yields and enantioselectivities (up to 92% yield, up to 94% ee). Deuterium-labelling experiments indicate that phenylphosphinic acid plays a pivotal role in the DKR of α-keto-β-lactams by promoting the enolization process. The synthetic potential of this protocol was demonstrated by its application in the synthesis of a key intermediate of Taxol and (+)-epi-Cytoxazone.  © 2020 The Royal Society of Chemistry 2020.

Citation Format(s)

Ni-Catalyzed asymmetric reduction of α-keto-β-lactams via DKR enabled by proton shuttling. / Wang, Fangyuan; Tan, Xuefeng; Wu, Ting et al.
In: Chemical Communications, Vol. 56, No. 99, 25.12.2020, p. 15557-15560.

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review