Synthesis and α-alkylation of 1-menthylphosphetane sulfide

Article abstract of DOI:10.1016/S0040-4020(97)00132-4

1-Menthylphosphetane sulfide, 5, has been prepared from menthylphosphine and 1-bromo-3-chloropropane via the corresponding phosphetane-borane complex. The metalation-substitution reactions of both intracyclic α carbon atoms of 5 with benzyl and/or trimethylsilyl groups have been examined with regard to stereochemistry. The diastereoselectivity of these reactions is high enough to allow a preparative access to new chiral phosphetane sulfides.