Premium
General Access to Modified α‐Amino Acids by Bioinspired Stereoselective γ‐C−H Bond Lactonization
Author(s) -
Vicens Laia,
Bietti Massimo,
Costas Miquel
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202007899
Subject(s) - amino acid , stereoselectivity , chemistry , catalysis , combinatorial chemistry , selectivity , manganese , stereochemistry , organic chemistry , biochemistry
α‐Amino acids represent a valuable class of natural products employed as building blocks in biological and chemical synthesis. Because of the limited number of natural amino acids available, and of their widespread application in proteomics, diagnosis, drug delivery and catalysis, there is an increasing demand for the development of procedures for the preparation of modified analogues. Herein, we show that the use of bioinspired manganese catalysts and H 2 O 2 under mild conditions, provides access to modified α‐amino acids via γ‐C−H bond lactonization. The system can efficiently target 1°, 2° and 3° γ‐C−H bonds of α‐substituted and achiral α,α‐disubstituted α‐amino acids with outstanding site‐selectivity, good to excellent diastereoselectivity and (where applicable) enantioselectivity. This methodology may be considered alternative to well‐established organometallic procedures.