Bifunctionalized Allenes. Part XIII. A Convenient and Efficient Method for Regioselective Synthesis of Phosphorylated a-Hydroxyallenes with Protected and Unprotected Hydroxy Group.

Molecules (Basel, Switzerland)

PubMedID: 24840901

Ismailov IE, Ivanov IK, Christov VCh. Bifunctionalized Allenes. Part XIII. A Convenient and Efficient Method for Regioselective Synthesis of Phosphorylated a-Hydroxyallenes with Protected and Unprotected Hydroxy Group. Molecules. 2014;19(5):6309-29.
The paper describes a convenient and efficient method for regioselective synthesis of phosphorylated a-hydroxyallenes using an atom economical [2,3]-sigmatropic rearrangement of intermediate propargyl phosphites or phosphinites. These can be readily prepared via reaction of protected alkynols with dimethyl chlorophosphite or chlorodiphenyl phosphine respectively in the presence of a base.