20
ORGANIC SYNTHESIS—1995
LA.5-16 van Oeveren, A. and Feringa, B.L., TL, 35, 8437; Schreiber,
S.L. et al., JACS, 116, 5505; Takacs, J.M. and Weidner, J.J., 70C, 59,
6480; see also: Ley, S.V. and Kouklovsky, C, Γ, 50, 835.
R
1
.
#
D ^ ^ T M S
HO.
R
2
QMe
7/
OMe
T1CI4, CH2CI2
2 ) H 2 0
34-87%
5:95 to 85:15
similarly with other leaving groups
I.A.5-17 Fish, P.V., TL, 35, 7181; see also: Overman, L.E. and
Renhowe, P.A., JOC, 59, 4138.
TMS
('PrOJTiCb
79-82%
similarly with an allyl stannane and EtAlCh
I.A.5-18 Hermans, B. and Hevesi, L., BSB, 103, 257; see also: Hirao,
T. et al., TL, 35, 8005.
R ^ S e M e
R*
SeMe
^TMS
SnCl 4
CH 2 C1 2
R
SeMe
25-69%
similar displacement of a benzylic sitane using VO(OEt)Cl2
ORGANIC SYNTHESIS—1995
LA.5-16 van Oeveren, A. and Feringa, B.L., TL, 35, 8437; Schreiber,
S.L. et al., JACS, 116, 5505; Takacs, J.M. and Weidner, J.J., 70C, 59,
6480; see also: Ley, S.V. and Kouklovsky, C, Γ, 50, 835.
R
1
.
#
D ^ ^ T M S
HO.
R
2
QMe
7/
OMe
T1CI4, CH2CI2
2 ) H 2 0
34-87%
5:95 to 85:15
similarly with other leaving groups
I.A.5-17 Fish, P.V., TL, 35, 7181; see also: Overman, L.E. and
Renhowe, P.A., JOC, 59, 4138.
TMS
('PrOJTiCb
79-82%
similarly with an allyl stannane and EtAlCh
I.A.5-18 Hermans, B. and Hevesi, L., BSB, 103, 257; see also: Hirao,
T. et al., TL, 35, 8005.
R ^ S e M e
R*
SeMe
^TMS
SnCl 4
CH 2 C1 2
R
SeMe
25-69%
similar displacement of a benzylic sitane using VO(OEt)Cl2