Synthesis and Enantioselective Aldol Reaction of a Chiral 2-Oxo-2-propionyl-1,3,2-oxazaphosphorinane

Article abstract of DOI:10.1021/jo00072a003

The synthesis of cis- and trans-2-oxo-2-propionyl-1,3,2-oxazaphosphorinane (cis- and trans-7), via the condensation of (S)-N-isopropyl-4-aminobutan-2-ol (5) with methyl dichlorophosphite (CH3OPCl2), followed by the Michaelis-Arbusov coupling with propionyl chloride is described, and our preliminary research involving metal-directed diastereo- and enantioselective aldol reactions between the lithio enolate of trans-oxazaphosphorinane 7 and benzaldehyde are also discussed.