Visible-Light-Mediated, Chemo- and Stereoselective Radical Process for the Synthesis of C-Glycoamino Acids

Peng Ji, Yueteng Zhang, Yongyi Wei, He Huang, Wenbo Hu, Patrick A. Mariano, Wei Wang

Research output: Contribution to journalArticlepeer-review

92 Scopus citations

Abstract

An approach for efficient synthesis of C-glycosyl amino acids is described. Different from typical photoredox-catalyzed reactions of imines, the new process follows a pathway in which α-imino esters serve as electrophiles in chemoselective addition reactions with nucleophilic glycosyl radicals. The process is highlighted by the mild nature of the reaction conditions, the highly stereoselectivity attending C-C bond formation, and its applicability to C-glycosylations using both armed and disarmed pentose and hexose derivatives.

Original languageEnglish (US)
Pages (from-to)3086-3092
Number of pages7
JournalOrganic Letters
Volume21
Issue number9
DOIs
StatePublished - May 3 2019

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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