Efficient method for selective introduction of substituents as C5 of isoleucine and other alpha-amino acids

Leleti Rajender Reddy; B V Subba Reddy; E J Corey

doi:10.1021/ol060952v

Efficient method for selective introduction of substituents as C5 of isoleucine and other alpha-amino acids

Org Lett. 2006 Jun 22;8(13):2819-21. doi: 10.1021/ol060952v.

Authors

Leleti Rajender Reddy¹, B V Subba Reddy, E J Corey

Affiliation

¹ Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.

PMID: 16774265
DOI: 10.1021/ol060952v

Abstract

[reaction: see text] A useful process for the position-selective remote bromination of N-trifluoroacetyl-alpha-amino esters is illustrated for the isoleucine case. The 5-bromoisoleucine derivative shown above can be used for the synthesis of many modified amino acids, as described herein.

MeSH terms

Amino Acids / chemistry*
Esters
Hydrocarbons, Brominated / chemistry*
Hydrocarbons, Chlorinated / chemistry
Isoleucine / chemistry*
Molecular Structure
Stereoisomerism

Substances

Amino Acids
Esters
Hydrocarbons, Brominated
Hydrocarbons, Chlorinated
Isoleucine