C3-symmetric trialkyl phosphites as starting compounds of asymmetric synthesis

✍ Scribed by Oleg I. Kolodiazhnyi; Sergey Sheiko; Evgeny V. Grishkun

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 178 KB
• Volume: 11
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/(sici)1098-1071(2000)11:2<138::aid-hc9>3.0.co;2-p

✦ Synopsis

Chiral C 3 -symmetric trialkyl phosphites, derivatives, of (‫1(-)מ‬R,2S,5R)-menthol, and (‫-)מ‬di-O-isopropylidene-1,2:5,6-␣-D-glucofuranose, have been studied as starting reagents for the preparation of chiral organophosphorus compounds. The reactions involve induction at the ␣-carbon atom of substituted ␣-alkylphosphonates. The stereoselectivity of the reaction depends on the structure of the starting compounds and the reaction conditions. The configurations of the alkylphosphonates were defined by means of NMR spectroscopy and by transformation into corresponding alkylphosphonic acids.