Russian Chemical Bulletin p. 1568 - 1573 (1999)
Update date:2022-08-05
Topics:
Kolodiazhnyi
Grishkun
Sheiko
Demchuk
Thoennessen
Jones
Schmutzler
Chiral C2-symmetrical dialkyl phosphites and C3-symmetrical trialkyl phosphites, derived from (-)-borneol, (-)-menthol, and 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, were studied as the starting reagents for the preparation of chiral organophosphorus compounds. The reactions of C2-symmetrical dialkyl phosphites and C3-symmetrical trialkyl phosphites with aldehydes and amines or aldehydes are accompanied by asymmetrical induction at the α-carbon atom to yield optically active α-aminoalkylphosphonates or α-hydroxyalkylphosphonates, respectively. The stereoselectivity of the reaction depends on the structure of the starting compounds and the reaction conditions.
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Doi:10.1021/jm00295a046
(1970)Doi:10.1007/BF00771468
()Doi:10.1016/S0040-4020(00)00084-3
(2000)Doi:10.1139/v98-231
(1999)Doi:10.1021/jo962423i
(1997)Doi:10.1080/00397919908086220
(1999)