CrCl 2 Mediated addition of allylic halides or phosphates to N-protected α-amino aldehydes. Stereocontrolled synthesis of a new core for C 2 symmetric HIV-protease inhibitors

Abstract

The addition of γ-monosubstituted allylchromium(III) reagents to N-protected α-amino aldehydes proceeds in a stereoconvergent manner in contrast with the case of the unsubstituted reagents, where the stereoselectivity depends on the nature of the group bonded to the nitrogen. The chromium(III) reagent derived from 3-chloromethyl-2-trimethylsilyl-1-propene was used to prepare a C 2 symmetric HIV-protease inhibitor.