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Paper | Regular issue | Vol 63, No. 12, 2004, pp.2797-2803
Published online, 26th October, 2004
DOI: 10.3987/COM-04-10222
Synthesis of 1,4:3,6-Dianhydro-D-mannitol 2,5-(Hydrogen Phosphate) and Its Usage in Palladium-catalyzed Hydroxycarbonylation of Styrene

Biao Jiang,* Zuo-Gang Huang, and Ke-Jun Cheng

*State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, 354 Finglin Road, Shanghai 200032, China

Abstract

Phosphorylation of 1,4:3,6-dianhydro-D-mannitol by phosphorus oxychloride in the presence of triethylamine followed by hydrolysis gave a cyclic hydrogen phosphate, which has the crystal structure of 6-hydroxy-6-oxo-2,5,7,10- tetraoxa-6-phospha-tricyclo[6.3.0.04,11]undecane. It was used as a chiral ligand in palladium-catalyzed hydroxycarbonylation of styrene. The regioselectivity was good, but the optical yield was limited.