Tetrahedron letters

Synthesis of chiral alkynes having 2 H or halogen at the secondary or tertiary propargylic stereogenic center by hydrolysis and halogenolysis of optically active …

DK An, S Okamoto, F Sato

Index: An, Duk Keun; Okamoto, Sentaro; Sato, Fumie Tetrahedron Letters, 1998 , vol. 39, # 25 p. 4555 - 4558

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Citation Number: 15

Abstract

The hydrolysis and halogenolysis of optically active allenyltitaniums, generated by the reaction of a Ti (Oi-Pr) 42 i-PrMgCl reagent with optically active propargyl alcohol derivatives, proceed in a regioselective way and with excellent degree of chiral transfer, thus opening up a highly efficient and practical route to chiral alkynes having 2H or Cl at the stereogenic propargylic center.