6 S. Kobayashi and S. Nagayama, J. Org. Chem., 1997, 62, 232;
S. Kobayashi and S. Nagayama, J. Am. Chem. Soc., 1997, 119,
0049; H. Nakamura, H. Iwama and Y. Yamamoto, J. Am. Chem.
Table 2 Results of the allylation with various aldimines
1
Soc., 1996, 118, 6641.
7
8
T. Akiyama, J. Takaya and H. Kagoshima, Chem. Lett., 1999, 947.
For reviews: H.-U. Reissig, In Organic Synthesis Highlights, ed. by
J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn and H.-U. Reissig,
VCH, Weinheim, 1991, p. 71; C.-J. Li, Chem. Rev., 1993, 93, 2023;
C.-J. Li and T.-H. Chan, Organic Reactions in Aqueous Media, John
Wiley & Sons, Inc.,New York, 1997; A. Lubineau, J. Auge and
Y. Queneau, Synthesis, 1994, 741; C.-J. Li, Tetrahedron, 1996, 52,
5643; Organic Synthesis in Water, ed. P. A. Grieco, Blackie
Academic & Professional, London, 1998; Modern Solvents in
Organic Synthesis, ed. P. Knochel, Springer, Berlin, 1999.
Entry
R
Ar
Ph
p-ClC H
p-ClC H
p-ClC H
p-ClC H
p-ClC H
p-ClC H
p-ClC H
p-ClC H
p-ClC H
p-ClC H
Yield (%)
1
2
3
4
5
6
7
8
9
Ph
Ph
p-ClC H
p-MeOC H
p-MeC H
85
86
83
87
82
69
69
82
69
6
4
4
4
4
4
4
4
4
4
4
4
6
4
6
9 S. Kobayashi, Eur. J. Org. Chem, 1999, 15.
10 T.-P. Loh, J. Pei and G.-Q. Cao, Chem. Commun., 1996, 1819.
11 T. Akiyama, J. Takaya and H. Kagoshima, Synlett, 1999, 1045.
12 T. Akiyama, J. Takaya and H. Kagoshima, Synlett, 1999, 1426;
T. Akiyama, J. Takaya and H. Kagoshima, Tetrahedron Lett., 2001,
42, 4025.
6
4
6
6
4
6
2-Thienyl
6
2-Furyl
Cyclohex
i-Pr
PhCH(CH3)
PhCH(CH3)
BnOCH(CH3)
6
6
6
b
1
1
1
0
1
2
68c
13 T. Akiyama, J. Takaya and H. Kagoshima, Tetrahedron Lett., 1999,
40, 7831.
6
84
6
d
p-ClC H
72
14 S. Kobayashi, T. Busujima and S. Nagayama, Chem. Commun.,
1998, 19.
15 W. Lu and T.-H. Chan, J. Org. Chem., 2000, 65, 8589.
6
a
d
b
c
Distilled water was employed. syn–anti = 85 : 15. syn–anti = 83 : 17.
syn–anti = 55 : 45.
1
6 Allylation of imine derivatives in the mixture of water and organic
solvent, see H. M. S. Kumar, S. Anjaneyulu, E. J. Reddy and
J. S. Yadav, Tetrahedron Lett., 2000, 41, 9311; S. Kobayashi, T.
Hamada and K. Manabe, Synlett, 2001, 1140.
References and notes
1
1
7 T. Akiyama, J. Takaya and H. Kagoshima, Chem. Lett., 1999, 947.
8 Recent example of the use of Lewis acid with water of crystalliz-
ation, see W. Zhuang, R. G. Hazell and K. A. Jørgensen, Chem.
Commun., 2001, 1240.
†
1
2
The IUPAC name for triflate is trifluoromethanesulfonate.
Y. Yamamoto and N. Asao, Chem. Rev., 1993, 93, 2207; R. Bloch,
Chem. Rev., 1998, 98, 1407.
H. Nakamura, K. Nakamura and Y. Yamamoto, J. Am. Chem. Soc.,
19 A typical experimental procedure for entry 1 of Table 2. Benzalde-
hyde (16 µl, 0.158 mmol) and aniline (22 µl, 0.241 mmol) were mixed
in degassed water (9.6 ml) under a N atmosphere for 1 h at room
2
1
998, 120, 4242; Y. Masuyama, J. Tosa and Y. Kurusu, Chem. Com-
temperature. SDS (18.0 mg, 0.064 mmol) and an aqueous solution
of tin() chloride dihydrate (18.0 mg, 0.080 mmol) in water (0.5 ml),
and allyltributylstannane (75 µl, 0.242 mmol) were added succes-
sively into the mixture. After being stirred at the temperature for
20 min, DOWEX1-X8 (100–200 mesh, Cl form), and sat. NaHCO3
solution KF solution were added to stop the reaction, and the
mixture was stirred for 5 min. The resultant solution was filtered
to remove the resin and the filtrate was extracted with ethyl acetate.
The combined organic layers were washed with brine, dried over
anhydrous Na SO , and concentrated to dryness. Purification of
mun., 1999, 1075; J. A. Marshall, K. Gill and B. M. Seletsky, Angew.
Chem., Int. Ed., 2000, 39, 953.
S. Kobayashi, S. Iwamoto and S. Nagayama, Synlett, 1997, 1099;
T. Gastner, H. Ishitani, R. Akiyama and S. Kobayashi, Angew.
Chem., Int. Ed., 2001, 40, 1896.
T. Akiyama and J. Iwai, Synlett, 1998, 273; T. Akiyama, J. Iwai,
Y. Onuma and H. Kagoshima, Chem. Commun., 1999, 2191.
S. J. Veenstra and P. Schmid, Tetrahedron Lett., 1997, 38, 997;
L. Mimi, K.-I. Serita, S. Hiraoka and T. Yokozawa, Tetrahedron
Lett., 2000, 41, 7075; M. Billet, P. Klotz and A. Mann, Tetrahedron
Lett., 2001, 42, 631.
3
4
5
2
4
the crude mixture by preparative TLC (SiO , hexane–ethyl acetate =
2
12 : 1, v/v) gave a homoallylic amine (29.8 mg) in 85% yield.
1
158
J. Chem. Soc., Perkin Trans. 1, 2002, 1157–1158