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Novel A-Hydroxyphosphonates - Enol Phosphates Rearrangement

Wróblewski A., Karolczak W.

Polish Journal of Chemistry

1999

vol. 73 nr 7

1191-1202

Chalcone epoxide derived hydroxyphosphonates - synthesis, stereochemistry and ring opening reactions

Wróblewski A.E., Karolczak W.

Polish Journal of Chemistry

1998

Vol. 72, nr 7

1160-1167

In the presece of KFx2H2O dimethyl phosphide adds preferentially (d.e. 50%) to the si face of the carbonyl group of chalcone epoxide. Under acidic conditions the oxirane ring in the major alpha-hydroxy-beta,gamma-epoxyphosphonate (1S*, 2S*, 3R*)-3a is regio- but not stereoselectively cleaved with methanol and/or water, while the minor one (1R*, 2S*, 3R*)-3b undergoes intramolecular cyclization to form 1,2-oxaphospholan-3,4-diols with full stereoselectivity.