O-N intramolecular alkoxycarbonyl migration of typical protective groups in hydroxyamino acids

Mariusz Skwarczynski; Youhei Sohma; Mayo Noguchi; Tooru Kimura; Yoshio Hayashi; Yoshiaki Kiso

doi:10.1021/jo0525579

O-N intramolecular alkoxycarbonyl migration of typical protective groups in hydroxyamino acids

J Org Chem. 2006 Mar 17;71(6):2542-5. doi: 10.1021/jo0525579.

Authors

Mariusz Skwarczynski¹, Youhei Sohma, Mayo Noguchi, Tooru Kimura, Yoshio Hayashi, Yoshiaki Kiso

Affiliation

¹ Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st COE Program, Kyoto Pharmaceutical University, Yamashina-ku, Kyoto 607-8412, Japan.

PMID: 16526815
DOI: 10.1021/jo0525579

Abstract

O-N Intramolecular alkoxycarbonyl (carbonate-carbamate) migration was found to occur as a common reaction of hydroxyamino acids under mild basic aqueous conditions with no formation of side products. Carbonate protective groups migrate to produce amino-protected carbamate derivatives of hydroxyamino acids with high efficiency and purity.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acids / chemistry*
Carbamates / chemistry*
Carbonates / chemistry*
Molecular Structure
Stereoisomerism

Substances

Amino Acids
Carbamates
Carbonates