Back to Search
Start Over
General Access to Modified α-Amino Acids by Bioinspired Stereoselective γ-C-H Bond Lactonization.
- Source :
-
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2021 Feb 23; Vol. 60 (9), pp. 4740-4746. Date of Electronic Publication: 2020 Dec 23. - Publication Year :
- 2021
-
Abstract
- 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 <subscript>2</subscript> O <subscript>2</subscript> 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.<br /> (© 2020 Wiley-VCH GmbH.)
Details
- Language :
- English
- ISSN :
- 1521-3773
- Volume :
- 60
- Issue :
- 9
- Database :
- MEDLINE
- Journal :
- Angewandte Chemie (International ed. in English)
- Publication Type :
- Academic Journal
- Accession number :
- 33210804
- Full Text :
- https://doi.org/10.1002/anie.202007899