Efficient method for selective introduction of substituents as C5 of isoleucine and other alpha-amino acids.
[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.
Reddy
Leleti Rajender
LR
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Reddy
B V Subba
BV
Corey
E J
EJ
D000596:Amino Acids / Q000737:chemistry*; D004952:Esters; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry; D007532:Isoleucine / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000596:Amino Acids; D004952:Esters; D006842:Hydrocarbons, Brominated; D006843:Hydrocarbons, Chlorinated; D007532:Isoleucine