Stereochemistry of nucleophilic substitution at trivalent phosphorus

GRAPHICAL ABSTRACT

ABSTRACT

Stereoselective reactions of achiral trivalent phosphorus compounds with chiral nucleophiles derived from secondary alcohols, amines, and aminoacids were described. The presented reactions provide an easy access to optically active aminophosphines and phosphinites, used as precursor compounds in the synthesis of chiral organophosphorus compounds. This reaction is convenient for studies of mechanism and stereochemistry of nucleophilic substitution at trivalent phosphorus.

KEYWORDS:

• Enantioselectivity
• diastereoselectivity
• chiral amines
• aminoacids
• chiral alcohols
• nucleophilic substitution