Abstract
The enolate anion of [CpMo(CO) 2 (η-CH 3 COC 3 H 4 )] (2), readily generated by lithium diisopropylamide in cold THF (-78°C), underwent alkylation with aldehydes to give the aldol products 3-5 in good yields. X-ray diffraction measurement of 3 shows strong intramolecular hydrogen bonding within the ketone and alcohol groups. The Me 4 NBH 4 reduction of 3-5 via proton-chelation control in benzene/CH 3 OH proceeded with fair diastereoselectivities in favor of the syn-1,3-diol. Addition of PhSNa to the NO + cation of the π-allyl syn-1,3-diols 6-8 gave (1R *,3S *)-1-R-4-((phenylthio)methyl)-4-pentene-1,3-diols (R = phenyl (9), furyl (10), tert-butyl (11). © 1994 American Chemical Society.