TY - JOUR
T1 - γ-Siloxy-benzyllithiums
T2 - Stereochemistry of the retro-[1,4]-Brook rearrangement
AU - Bousbaa, J.
AU - Ooms, F.
AU - Krief, A.
PY - 1997/10/27
Y1 - 1997/10/27
N2 - Although γ-sulfonyloxy-benzylselenides react with butyllithium to produce stereospecifically aryl cyclopropanes, the corresponding γ-silyloxy-benzylselenides lead to a stereoisomeric mixture of γ-hydroxy-α-silyl-benzylselenides via the retro-[1,4]-Brook rearrangement. Apparently the intermediate benzyllithiums are alkylated before epimerisation takes place in the first case, whereas in the second one epimerisation occurs prior to the silyl group migration.
AB - Although γ-sulfonyloxy-benzylselenides react with butyllithium to produce stereospecifically aryl cyclopropanes, the corresponding γ-silyloxy-benzylselenides lead to a stereoisomeric mixture of γ-hydroxy-α-silyl-benzylselenides via the retro-[1,4]-Brook rearrangement. Apparently the intermediate benzyllithiums are alkylated before epimerisation takes place in the first case, whereas in the second one epimerisation occurs prior to the silyl group migration.
UR - http://www.scopus.com/inward/record.url?scp=0030816226&partnerID=8YFLogxK
U2 - 10.1016/S0040-4039(97)01810-8
DO - 10.1016/S0040-4039(97)01810-8
M3 - Article
AN - SCOPUS:0030816226
SN - 0040-4039
VL - 38
SP - 7625
EP - 7628
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 43
ER -