Direct Synthesis of Chiral NH Lactams via Ru-Catalyzed Asymmetric Reductive Amination/Cyclization Cascade of Keto Acids/Esters

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

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Author(s)

  • Yongjie Shi
  • Shuang Gao
  • Yao Zhang
  • Jingxin Wang
  • Xumu Zhang
  • Qin Yin

Detail(s)

Original languageEnglish
Pages (from-to)2707-2713
Journal / PublicationOrganic Letters
Volume22
Issue number7
Online published19 Mar 2020
Publication statusPublished - 3 Apr 2020
Externally publishedYes

Abstract

Lactams with a stereogenic center adjacent to the N atom have existed in many medicinal agents and bioactive alkaloids. Herein we report a broadly applicable synthesis of enantioenriched NH lactams through a one-pot asymmetric reductive amination/cyclization sequence of easily available keto acids/esters. Such cascade processes alleviate the demand for protecting group manipulations as well as intermediate purification. This strategy is capable of constructing enantioenriched lactams and benzo-lactams of a five-, six-, or seven-membered ring in generally high yield and with excellent enantioselectivities (up to 97% ee). Scalable and concise syntheses of key drug intermediates have further displayed the importance of this methodology. Copyright © 2020 American Chemical Society.

Citation Format(s)

Direct Synthesis of Chiral NH Lactams via Ru-Catalyzed Asymmetric Reductive Amination/Cyclization Cascade of Keto Acids/Esters. / Shi, Yongjie; Tan, Xuefeng; Gao, Shuang et al.
In: Organic Letters, Vol. 22, No. 7, 03.04.2020, p. 2707-2713.

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