Ir-Catalyzed Asymmetric Hydrogenation of α-Alkylidene β-Lactams and Cyclobutanones

Jingzhao Xia, Yu Nie, Guoqiang Yang, Yangang Liu, Ilya D. Gridnev, Wanbin Zhang

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

Chiral β-lactams and cyclobutanones are present in numerous natural and pharmaceutical products. The stereoselective construction of chiral four-membered cyclic compounds is an ongoing challenge for the chemical community. Herein, we report a highly stereocontrolled construction of four-membered ring (mini-sized) β-lactams and cyclobutanones via an Ir/In-BiphPHOX-catalyzed asymmetric hydrogenation, providing the corresponding optically active four-membered ring carbonyl products bearing an α-chiral carbon center with excellent yields (up to 99%) and enantioselectivities (up to 98%) under mild reaction conditions (1.0—2.5 bar H2 for 1.0—10 h). The reaction presents wide substrate scope. Diverse transformations of the catalyzed products were also conducted to show the potential utility of this protocol.

Original languageEnglish
Pages (from-to)612-618
Number of pages7
JournalChinese Journal of Chemistry
Volume36
Issue number7
DOIs
Publication statusPublished - 2018 Jul 1

Keywords

  • asymmetric hydrogenation
  • cyclobutanone
  • iridium
  • phosphine-oxazoline ligand
  • β-lactam

ASJC Scopus subject areas

  • Chemistry(all)

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