Convenient synthesis of L-proline benzyl ester.
Mesylates or tosylates of delta-hydroxy-L-norvaline esters spontaneously afford L-proline esters upon exposure to aqueous buffer in near quantitative yield. This novel reaction has led to the development of a simple route to optically active proline esters.
Córdova
A
A
Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037, USA.
Reed
N N
NN
Ashley
J A
JA
Janda
K D
KD
D000476:Alkanesulfonates / Q000737:chemistry; D001190:Arylsulfonates / Q000737:chemistry; D001593:Benzyl Compounds / Q000138:chemical synthesis*; D008698:Mesylates / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D014633:Valine / Q000031:analogs & derivatives / Q000737:chemistry
D000476:Alkanesulfonates; D001190:Arylsulfonates; D001593:Benzyl Compounds; D008698:Mesylates; C052594:proline benzyl ester; D011392:Proline; C005313:norvaline; D014633:Valine