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2005
Organo-phosphorus compounds
S 0080
Syntheses of ω-Hydroxy-α,α-difluoromethylphosphonates by Oxacycle
Reactions. — The first one-step synthesis of a variety of δ-, γ-, and
05- 164 Ring-Opening
ω-hydroxy-α,α-difluoromethylphosphonates is developed from a non-HCFC-based
source of phosphonodifluoromethyl carbanion, through oxacycle ring-opening reactions. The use of BF3-Et 2O as Lewis acid is essential as well as the excess of epoxide
in the reaction with (II) or the excess of a carbanion in the reaction with (IV). The
ring-opening reactions are easily performed from epoxides, oxetane, and THF to prepare important pivotal structures for the design of enzyme inhibitors in one step. The
reaction with tetrahydropyran is unsuccessful and phosphonate (X) is the sole product
observed. — (OZOUF, P.; BINOT, G.; POMMELET, J.-C.; LEQUEUX*, T. P.; Org.
Lett. 6 (2004) 21, 3747-3750; Lab. Chim. Mol. Thio-Org., CNRS, Inst. Sci. Matiere
Rayonnem., Univ. Caen, F-14050 Caen, Fr.; Eng.) — Steudel
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