Tetrahedron p. 7435 - 7463 (1996)
Update date:2022-08-03
Topics:
Krief, Alain
Kenda, Benoit
Remacle, Bruno
2-Ethyl-1-methyl-1-phenyl cyclopentane, unavailable by butyllithium-promoted carbocyclisation of the corresponding alkenyl selenide, has been synthesized from 6-methylseleno-6-phenyl-1-phenylthio-1-heptene and 7-methylseleno-7-phenyl-2-phenylthio-2-octene with high stereocontrol at all the three stereogenic centers. Depending upon the solvent used, the derivative in which the methyl- and the phenylthiomethyl groups are cis (in THF) or trans (in pentane) to each other are formed selectively.
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