TY - JOUR
T1 - Stereoselective syntheses of 1,2-dialkyl-1-phenyl cyclopentanes involving intramolecular carbolithiation of α-thioalkenes
AU - Krief, A.
AU - Kenda, B.
AU - Remacle, B.
PY - 1996/5/20
Y1 - 1996/5/20
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0029986825&partnerID=8YFLogxK
U2 - 10.1016/0040-4020(96)00261-X
DO - 10.1016/0040-4020(96)00261-X
M3 - Article
AN - SCOPUS:0029986825
SN - 0040-4020
VL - 52
SP - 7435
EP - 7463
JO - Tetrahedron
JF - Tetrahedron
IS - 21
ER -