Oi. Kolodiazhnyi et al., Asymmetric synthesis of alpha-substituted alkylphosphonates based on symmetrical dialkyl phosphites, RUSS CHEM B, 48(8), 1999, pp. 1568-1573
Chiral C-2-symmetrical dialkyl phosphites and C-3-symmetrical trialkyl phos
phites, derived from (-)-borneol, (-)-menthol, and 1,2:5,6-di-O-isopropylid
ene-alpha-D-glucofuranose, were studied as the starting reagents for the pr
eparation of chiral organophosphorus compounds. The reactions of C-2-symmet
rical dialkyl phosphites and C-3-symmetrical trialkyl phosphites with aldeh
ydes and amines or aldehydes are accompanied by asymmetrical induction at t
he alpha-carbon atom to yield optically active alpha-aminoalkylphosphonates
or alpha-hydroxyalkylphosphonates, respectively. The stereoselectivity of
the reaction depends on the structure of the starting compounds and the rea
ction conditions.