In 1978, Stec and Krzyzanowska described a new route to primary amines based on the chemistry of N-diphenylphosphinyl imines [ 1,2]. These novel imine derivatives were prepared from the corresponding oximes by treatment with cholorodiphenylphosphine and triethylamine (Scheme 1). Unlike the oximes from which they are derived, the phosphinyl imines possess an electrophilic imine carbon and undergo facile reduction with sodium borohydride. The overall sequence is complementary to the reductive amination of the parent carbonyl compounds. Other nucleophiles such as cyanide ion and Grignard reagents were shown to add to N-phosphinyl imines [1], and both diastereoselective and enantioselective reductions with hydride reagents have been described by Hutchins and co-workers [3,4]. We became interested in the potential synthetic applications of carbohydrate-derived N-phosphinyl imines during the course of our studies of amino and nitro sugar synthesis. Herein we describe the preparation and ~ =: NOH O 0 i, Ph2PCI ~:== II NaBH4 ~NHPPh2 H+ ~..ssNH2 NPPh2 ~ /'"/H ~ H Scheme 1. reduction of carbohydrate N-phosphinyl imines of 3-deoxy-l,2:5,6-di-O-isopropylidenea-D-glucofuranose-3-ulose oxime (1) and methyl 4,6-O-benzylidene-2,3-dideoxy-c~-~ erythro-hexopyranosid-3-ulose oxime (2).