Design of Photoredox-Catalyzed Giese-Type Reaction for the Synthesis of Chiral Quaternary α-Aryl Amino Acid Derivatives via Clayden Rearrangement

Peng Ji, Jing Chen, Xiang Meng, Feng Gao, Yue Dong, Hang Xu, Wei Wang

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Chiral quaternary α-aryl amino acids are biologically valued but synthetically challenging building blocks. Herein, we report a strategy for the synthesis of molecular architectures by unifying a photoredox catalytic asymmetric Giese-type reaction and Clayden rearrangement. A new class of chiral Karady-Beckwith dehydroalanines is designed and serves as a versatile handle for the photoredox-mediated highly stereoselective Giese-type reaction with feedstock carboxylic acids and tertiary amines. Subsequent Clayden rearrangement delivers chiral quaternary α-aryl amino acid derivatives with high stereoselectivity. The versatile approach offers a reliable source for the assembly of highly demanding chiral building blocks.

Original languageEnglish (US)
Pages (from-to)14706-14714
Number of pages9
JournalJournal of Organic Chemistry
Volume87
Issue number21
DOIs
StatePublished - Nov 4 2022

ASJC Scopus subject areas

  • Organic Chemistry

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