SYNTHESIS AND ALPHA-ALKYLATION OF 1-MENTHYLPHOSPHETANE SULFIDE

1-Menthylphosphetan sulfide, 5, has been prepared from menthylphosphin e and 1-bromo-3-chloropropane via the corresponding phosphetane-borane complex. The metalation-substitution reactions of both intracyclic al pha carbon atoms of 5 with benzyl and/or trimethylsilyl groups have be en examined with regard to stereochemistry. The diastereoselectivity o f these reactions is high enough to allow a preparative access to new chiral phosphetane sulfides. (C) 1997 Elsevier Science Ltd.