HIGHLY ENANTIOSELECTIVE AMIDE LIGATION BY PRIOR THIOL CAPTURE

Article abstract of DOI:10.1016/0040-4039(91)80674-U

The mixed disulfides from (R,S)-1-(Cbz-L-alanyloxy)-9-mercapto-phenoxathiin-10-sulfoxide and H-L-Cys-OMe undergo O,N-acyl transfer in DMSO at 23 deg C with rate constants of 7.0 h^-1 and 0.048 h^-1, and a rate ratio of 146; EM values of 0.2 M and 0.015 M.