70
ORGANIC SYNTHESIS—1995
LB. Carbon-Carbon Double Bonds
(see also: I.E.I)
I.B.I. Wittig-Tvoe Olefination Reactions
LB. 1-1 Dondoni, A. et al., JACS, 116, 3324; Hase, T. et al., SL, 817;
Wei, Z.Y. and Knaus, E.E., SL, 345.
RCHO + p h p
i
s
O
N
CHCU
I.B.1-2 Aurich, H.G. and Quintero, J.-L.R., T, 50, 3943; McKervey,
M.A. et al., CC, 1220.
HO L C0 2 Et
O *"
+ Ph 3 P=CHCN
C0 2 Et
THF
S
reflux, 2h
HO
'Pr
CN
E = 41%
Z = 30%
LB.1-3 Denmark, S.E. and Rivera, I., JOC, 59, 6887; Furuta, T. and
Iwamura, M., CC, 2167; Rein, T., Reisen, O. et al, AG(E), 33, 556.
X 0 2 M e
0 ^ P ;
C0 2 Me
O
KHMDMS
THF, -35°C
V
R
78-86%
e.e. = 78-86%