CRCL2 MEDIATED ADDITION OF ALLYLIC HALIDES OR PHOSPHATES TO N-PROTECTED ALPHA-AMINO ALDEHYDES - STEREOCONTROLLED SYNTHESIS OF A NEW CORE FOR C-2 SYMMETRICAL HIV-PROTEASE INHIBITORS

The addition of gamma-monosubstituted allylchromium(lll) reagents to N -protected alpha-amino aldehydes proceeds in a stereoconvergent manner in contrast with the case of the unsubstituted reagents, where the st ereoselectivity depends on the nature of the group bonded to the nitro gen. The chromium(III) reagent derived from 3-chloromethyl-2-trimethyl silyl-1-propene was used to prepare a C-2 symmetric HIV-protease inhib itor. Copyright (C) 1996 Elsevier Science Ltd