Chemo- and Enantioselective Hydrogenation of α-Formyl Enamides: An Efficient Access to Chiral α-Amido Aldehydes

Jian Zhang, Jia Jia, Xincheng Zeng, Yuanhao Wang, Zhenfeng Zhang, Ilya D. Gridnev, Wanbin Zhang

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

In order to effectively synthesize chiral α-amino aldehydes, which have a wide range of potential applications in organic synthesis and medicinal chemistry, a highly chemo- and enantioselective hydrogenation of α-formyl enamides has been developed, catalyzed by a rhodium complex of a P-stereogenic bisphosphine ligand. Under different hydrogen pressures, the chiral α-amido aldehydes and β-amido alcohols were obtained in high yields (97–99 %) and with excellent chemo- and enantioselectivities (up to >99.9 % ee). The hydrogenation can be carried out on a gram scale and with a high substrate/catalyst ratio (up to 20 000 S/C), and the hydrogenated products were further converted into several important chiral products. Computations of the catalytic cycle gave a clear description for the R/S pathways, provided a reasonable explanation for the enantioselectivity, and revealed several other specific features.

Original languageEnglish
Pages (from-to)11505-11512
Number of pages8
JournalAngewandte Chemie - International Edition
Volume58
Issue number33
DOIs
Publication statusPublished - 2019 Aug 12

Keywords

  • chemoselectivity
  • enantioselectivity
  • homogeneous catalysis
  • hydrogenation

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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