4
30 Letters in Organic Chemistry, 2011, Vol. 8, No. 6
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(a) Keck, G. E.; Enholm, E. J. Homoallylamines from aldimines
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Iwama, H.; Yamamoto, Y. Palladium- and platinum- catalyzed
addition of aldehydes and imines with allylstannanes.
chemoselective allylation of imines in the presence of aldehydes. J.
Am. Chem. Soc. 1996, 118, 6641. (c) Nakamura, H.; Bao, M.;
1
H), 6.23 (d, 1H, J = 8.0 Hz), 6.59 (t, 1H, J = 7.6 Hz), 6.67
(
t, 1H, J = 7.6 Hz ), 6.72 (d, 1H, J = 4.4 Hz), 7.55 (d, 2H, J =
9
.2 Hz), 8.18 (d, 2H, J = 8.4 Hz) ppm.
1
Compound (1g): H NMR (CDC1
3
) ꢀ 2.57-2.62 (m, 2H),
4
1
.48 (t, 1H, J = 6.8 Hz), 5.17-5.23 (m, 2H), 5.73-5.78 (m,
H), 6.27 (d, 1H, J = 7.6 Hz), 6.55-6.59 (m, 1H), 6.64-6.70
3
Yamamoto, Y. The rate of bis(ꢁ -allyl)palladium complexes in the
presence of aldehydes (or imines) and allylic chlorides: stille
coupling versus allylation of aldehydes (or imines). Angew. Chem.
Int. Ed. Engl. 2001, 40, 3208. (d) Kobayashi, S. Lanthanides:
Chemistry and Use in Organic Synthesis; Springer-Verlag:
Heidelberg, Germany, 1999. (e) Manabe, K.; Mori, Y.; Kobayashi,
S. Three-component carbon-carbon bond-forming reactions
catalyzed by a Brønsted acid-surfactant combined catalyst in water.
Tetrahedron 2001, 57, 2537. (f) Kobayashi, S.; Nagayama, S.
Aldehydes vs aldimines. unprecedented aldimine-selective
nucleophilic additions in the coexistence of aldehydes using a
lanthanide salt as a Lewis acid catalyst. J. Am. Chem. Soc. 1997,
119, 10049. (g) Akiyama, T.; Onuma, Y. Tin(II) chloride mediated
allylation of aldimines generated in situ with allylstannane in water.
J. Chem. Soc. Perkin Trans 1 2002, 1157. (h) Yadav, J. S.; Reddy,
(
7
m, 1H), 6.72 (d, 1H, J = 7.6 Hz), 7.47 (t, 1H, J = 8.0 Hz),
.72 (d, 1H, J = 7.6 Hz), 8.08 (dd, 1H, J = 1.6, 8.0 Hz), 8.24
(
dd, 1H, J = 1.6, 4.0 Hz) ppm.
1
Compound (2h): H NMR (CDC1
3
) ꢀ2.50-2.60 (m, 2H),
4
1
.36 (t, 1H, J = 7.6 Hz), 5.13-5.21 (m, 2H), 5.71-5.76 (m,
H), 6.34 (d, 1H, J = 8.0 Hz), 6.60 (t, 1H, J = 7.6 Hz), 6.72
(
d, 2H, J = 8.0 Hz), 7.26-7.31 (m, 4H) ppm.
1
Compound (1i): H NMR (CDC1
3
) ꢀ 2.43-2.50 (m, 2H),
3
1
2
.73 (s, 3H) 5.14-5.20 (m, 2H), 5.81-5.89 (m, 1H), 6.19 (dd,
H, J = 6.0, 15.5 Hz), 6.57-6.64 (m, 3H), 6.75 (dd, 2H, J =
.5, 6.5 Hz), 7.19-7.36 (m, 5H) ppm.
1
4
B. V. S.; Reddy, R. S. R.; Rao, M. S. LiClO -catalyzed three-
component- coupling reactions: a facile synthesis of homoallylic
amines. Tetrahedron Lett. 2002, 43, 6245. (i) Yadav, J. S.; Reddy,
B. V. S.; Raju, A. K.; Gnaneshwar, D. Montmorillonite clay-
catalyzed three-component coupling reactions: A facile synthesis of
homoallylic amines. Adv. Synth. Catal. 2002, 344, 938.
Zhang, X, -X. MgI Etherate-promoted allylation of aldehydes:
2
simple and efficient synthesis of homoallylic alcohols. Lett. Org.
Chem. 2007, 4, 246.
Arkley, V.; Attenburrow, J.; Gregory, G. I.; Talker, W.
Griseofulvin analogues. Part I. Modification of the aromatic ring. J.
Chem. Soc. 1962, 1260.
Bloch, R. Additions of organometallic reagents to C=N bonds:
reactivity and selectivity. Chem. Rev. 1998, 98, 1407.
(a) Denmark, S. E.; Stavenger, R. A. Asymmetric catalysis of aldol
reactions with chiral Lewis bases. Acc. Chem. Res. 2000, 33, 432.
(b) Denmark, S. E.; Wynn, T. Lewis base activation of Lewis
acids: Catalytic enantioselective allylation and propargylation of
aldehydes. J. Am. Chem. Soc. 2001, 123, 6199.
Bellucci, C; Cozzi, P. G.; Achille; U. R. Catalytic allylation of
imines promoted by lanthanide triflates. Tetrahedron.Lett. 1995,
36, 7289.
Xie, Z. F.; Li, G. L.; Zhao, G.; Wang, J. D. Three-component
synthesis of homoallylic amines catalyzed by phosphomolybdic
acid in water. Chin. J. Chem. 2009, 27, 925.
3
Compound (1j): H NMR (CDC1 ) ꢀ 2.64 -2.67 (m, 2H),
3
5
=
.98 (br s, 1H), 4.55 (t, 1H, J = 6.5 Hz), 5.12-5.19 (m, 2H),
.71-5.79 (m, 1H), 6.16 (d, 1H, J = 3.5 Hz), 6.28 (dd, 1H, J
1.5, 3.0 Hz), 6.60 (dd, 2H, J = 1.0, 8.5 Hz), 6.70 (t, 1H, J =
[6]
[7]
7
.5 Hz), 7.14 (dd, 2H, J = 7.0, 9.0 Hz), 7.34 (s, 1H) ppm.
1
Compound (1k): H NMR (CDC1
3
) ꢀ 2.64-2.68 (m, 2H),
4
5
1
.12 (br s, 1H), 4.71 (t, 1H, J = 7.5 Hz), 5.15-5.21 (m, 2H),
.76-5.83 (m, 1H), 6.60 (d, 2H, J = 7.5 Hz), 6.68-6.71 (m,
H), 6.93-6.98 (m, 2H), 7.11-7.17 (m, 3H) ppm.
1
[
8]
[9]
3
Compound (1l): H NMR (CDC1 ) ꢀ 2.52-2.55 (m, 2H),
3
1
.62(d, 1H, J = 13.0 Hz), 3.81(d, 1H, J = 13.5 Hz), 4.02 (t,
H, J = 7.0 Hz), 5.05-5.12 (m, 2H), 5.67-5.76 (m, 1H), 6.97
(
t, 1H, J = 3.0, 5.0 Hz), 7.24-7.26 (m, 2H), 7.29-7.33 (m,
[10]
4
H) ppm.
1
Compound (1m): H NMR (CDC1
3
) ꢀ 1.77-1.90 (m, 2H),
[
11]
2
1
6
7
.32 (t, 2H, J = 6.5 Hz), 2.70-2.76 (m, 2H), 3.34-3.39 (m,
H), 3.75 (s, 3H), 5.05-5.10 (m, 2H), 5.76-5.84 (m, 1H),
.55 (d, 2H, J = 8.5 Hz), 6.76 (dd, 2H, J = 2.0, 6.5 Hz), 7.16-
.20 (m, 3H), 7.26-7.29 (m, 2H) ppm.
[12]
Law, M. C.; Cheung ,T. W.; Wong, K.;Yind Chan, T. H . Synthetic
and mechanistic studies of indium-mediated allylation of imines in
ionic liquids. J. Org. Chem. 2007, 72, 923.
[
13]
14]
Boyapati, M. C.; Karangula; J.; Sateesh; M.; Mannepalli, L. K.
Allylation of aldehydes, aldimines and ring opening of terminal
aromatic epoxides by scandium triflate using polyethylene glycol
ACKNOWLEDGEMENT
(
PEG) as an efficient recyclable medium. Synlett. 2004, 231.
Financial support from the Zhejiang Province Natural
Science Foundation of China (Project Y4100692).
[
Li, X.; Liu, X. -H.; Fu, Y. -Z.; Wang, L. -J.; Zhou, L.; Feng, X.-M.
Direct allylation of aldimines catalyzed by C -symmetric N,N’-
dioxide–Sc complexes: highly enantioselective synthesis of
2
III
homoallylic amines. Chem. Eur. J. 2008, 14, 796.
Li, L.; Zhao, G.. Allylation of aldehydes and imines: promoted by
reuseable polymer-supported sulfonamide of N-glycine. Org. Lett.
2006, 8, 633.
[
[
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