CARBON-CARBON BOND FORMING REACTIONS
49
I.A.7.a.4-4 Sturino, CF. and Fallis, A.G., JACS, 116, 7447; LeGall, T.
et al., TL, 35, 6671; Inanaga, J. et al., SL, 377; Shono, T. et al., JOC, 59,
1730.
Ph 2 Nv 'N
O
NHNPh,
K ^ .
SmI,
THF,HMPA
n = 4
a"OH
58-62%, cisrtrans = 25:1
similar pinacol-type couplings with dialdehydes or ketones /
Sm(OTf)2 or by electrolysis of ketones & O-methyloximes
I.A.7.a.4-5 Szymoniak, J. et al., T, 50, 2841.
H B
NbCl,
RCHO
THF, rt
rf
1
D
« O H R
\
^.OH
19-71%
dl : meso =
9:1 to >95:5
R
»
0-59%
dl : meso + meso'
9:1 to 94:6
I.A.7.a.4-6 Iqbal, J. et al., TL, 35, 2959.
N^ ^CHO
σ
Co", 0 2
PrCHO
90%
49
I.A.7.a.4-4 Sturino, CF. and Fallis, A.G., JACS, 116, 7447; LeGall, T.
et al., TL, 35, 6671; Inanaga, J. et al., SL, 377; Shono, T. et al., JOC, 59,
1730.
Ph 2 Nv 'N
O
NHNPh,
K ^ .
SmI,
THF,HMPA
n = 4
a"OH
58-62%, cisrtrans = 25:1
similar pinacol-type couplings with dialdehydes or ketones /
Sm(OTf)2 or by electrolysis of ketones & O-methyloximes
I.A.7.a.4-5 Szymoniak, J. et al., T, 50, 2841.
H B
NbCl,
RCHO
THF, rt
rf
1
D
« O H R
\
^.OH
19-71%
dl : meso =
9:1 to >95:5
R
»
0-59%
dl : meso + meso'
9:1 to 94:6
I.A.7.a.4-6 Iqbal, J. et al., TL, 35, 2959.
N^ ^CHO
σ
Co", 0 2
PrCHO
90%