48
ORGANIC SYNTHESIS—1995
I.A,7,a.4. Other 1.2-Additions
LA.7.a.4-l Kiljunen, E. and Kanerva, L.T., TA, 5, 311; Davis, F.A.
Deutsch, CJ. et al, S, 701.
a
C H O
i)
,
-,
-
^
—
"
'
Ο Η
84% conversion, 90% ee
1) acetone cyanohydrin, Sorghum bicolor shoots,
diisopropyl ether
preparation of an aminonitrile via TMSCN reaction with an imine
also reported
I.A.7.a.4-2 Scholl, M. and Fu, G.C., JOC, 59, 7178.
Bu 3 SnCN
>OSiEt 3
RCHO + Et 3 SiCN
1 ►
R H C \
20°C
N
CN
79-99%
I.A.7.a.4-3 McMurry, J.E. and Siemers, N.O., TU 35, 4505; Nicolaou,
K.C. et al., JACS, 116, 1591; Swindell, C.S. et al., TL, 35, 4959; see
also: Li, Y. et al., S, 678; Pedersen, S.F. et al., JACS, 116, 1316;
Kammermeier, B., Jendralla, H. et al., AG(E), 33, 685.
f^ r
CHO
™ ^ , ,
fP\
^ Ν ^ ^ ^ γ ^
Zn/Cu
^ χ ^ ^ Λ ^
11
>60% '
similarly with VCI3 / Zn
ORGANIC SYNTHESIS—1995
I.A,7,a.4. Other 1.2-Additions
LA.7.a.4-l Kiljunen, E. and Kanerva, L.T., TA, 5, 311; Davis, F.A.
Deutsch, CJ. et al, S, 701.
a
C H O
i)
,
-,
-
^
—
"
'
Ο Η
84% conversion, 90% ee
1) acetone cyanohydrin, Sorghum bicolor shoots,
diisopropyl ether
preparation of an aminonitrile via TMSCN reaction with an imine
also reported
I.A.7.a.4-2 Scholl, M. and Fu, G.C., JOC, 59, 7178.
Bu 3 SnCN
>OSiEt 3
RCHO + Et 3 SiCN
1 ►
R H C \
20°C
N
CN
79-99%
I.A.7.a.4-3 McMurry, J.E. and Siemers, N.O., TU 35, 4505; Nicolaou,
K.C. et al., JACS, 116, 1591; Swindell, C.S. et al., TL, 35, 4959; see
also: Li, Y. et al., S, 678; Pedersen, S.F. et al., JACS, 116, 1316;
Kammermeier, B., Jendralla, H. et al., AG(E), 33, 685.
f^ r
CHO
™ ^ , ,
fP\
^ Ν ^ ^ ^ γ ^
Zn/Cu
^ χ ^ ^ Λ ^
11
>60% '
similarly with VCI3 / Zn