TY - JOUR TI - Sequential asymmetric dihydroxylation and sulfoxidation of homoallylic sulfides. Stereochemical aspects of the preparation of new trifunctional chiral building blocks AU - Skarżewski, J. AU - Wojaczyńska, E. AU - Turowska-Tyrk, I. T2 - Tetrahedron Asymmetry AB - Products with three new stereogenic centers were generated via sequential asymmetric dihydroxylation and sulfoxidation of homoallylic sulfides. The non-racemic homoallylic sulfoxides were prepared using chiral, vanadyl-based catalytic system with e.e. of up to 85%. Subsequently, these compounds were dihydroxylated with AD-mix system and gave products of low d.e.s (up to 40%). Recrystallization of l-diastereomers furnished both enantiomerically pure 1-phenyl-4-phenylsulfinylbutane-1,2-diols (X-ray), which are new and useful chiral building blocks. Further oxidation at sulfur produced the corresponding enantiomers of 1-phenyl-4-phenylsulfonylbutane-1,2-diol. © 2002 Elsevier Science Ltd. All rights reserved. DA - 2002/// PY - 2002 DO - 10.1016/S0957-4166(02)00123-4 DP - Scopus VL - 13 IS - 4 SP - 369 EP - 375 DB - Scopus ER -