HYDROXYL-DIRECTED REDUCTION OF BETA-HYDROXYCYCLOALKANONES AS A STEREOSELECTIVE ROUTE TO 1,3-DIOLS - X-RAY CRYSTAL-STRUCTURE AND STRUCTURAL FEATURES OF (1R-ASTERISK,2R-ASTERISK,6S-ASTERISK)-2-[HYDROXY(PHENYL)METHYL]CYCLOPENTANOL

syn and anti Aldol adducts 4/5 and 6/7 undergo reduction using NaBH(OAc)(3) to give 1,3-diols with good to excellent levels of diastereoselectivity. Reduction using NaBH4 is generally less selective but, in the cyclohexyl series, reduction of the syn aldol adduct 6 does afford a complementary stereochemical outcome in relation to the product 1,3-diols obtained, 12 vs. 13. The structure of the diol 9 has been determined by X-ray crystallographic analysis, thereby providing proof of the stereochemical course of the reduction of the aldol 4. Additionally, the diol 9 is shown to pack in the solid state as columnar stacks of independent hexamers with each pillar comprising a central (OH)(6) core, incorporating a network of hydrogen bonds, with a hydrophobic exterior.