Variation of the C1 Component in the Silicon-Induced Domino Synthesis of Cyclopentanes

Article abstract of DOI:10.1016/S0040-4020(98)00697-8

The reaction of mono- or bissilylated thioanisole derivatives 2b-e with 3,4-epoxybutyl tosylate (3) affords the cyclopentanols 6a-c. Migratory aptitudes of two different silyl groups in the Brook 1,4-rearrangement is examined starting from 2d, e giving the order SiMe2Ph > SiMe3 > SiMePh2. The relative configuration of the resulting 1,3-functionalized cyclopentanes is established by NOE experiments after derivatization of the alcohol to the corresponding pivalates 7a-c.