Tetrahedron p. 11481 - 11488 (1998)
Update date:2022-08-03
Topics:
Braeuer, Nico
Michel, Tycho
Schaumann, Ernst
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.
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