Abstract
A highly selective, three-component reaction promoted by carboxylic acids for the synthesis of homoallylic amines has been developed. By using maleic acid or trifluoroacetic acid as a promoter, the reaction between a variety of aldehydes, aromatic amines, and allyltin reagents proceeds smoothly to afford the corresponding homoallylic amines in moderate to quantitative yields under mild conditions.
Key words
allylations - carboxylic acids - imines - multicomponent reactions - tin
References
1a Davies AG.
Organotin Chemistry
Wiley-VCH;
Weinheim:
2004.
1b Hisashi Y.
Koichiro O.
Main Group Metals in Organic Synthesis
Vol. 2:
Wiley-VCH;
Weinheim:
2004.
p.621-720
1c Junzo O.
Modern Carbonyl Chemistry
Wiley-VCH;
Weinheim:
2000.
1d Marshall JA.
Chem. Rev.
2000,
100:
3163
1e Marshall JA.
Chem. Rev.
1996,
96:
31
1f Yamamoto Y.
Asao N.
Chem. Rev.
1993,
93:
2207
1g Nishigaichi Y.
Takuwa A.
Naruta Y.
Maruyama K.
Tetrahedron
1993,
49:
7395
2a Keck GE.
Enholm EJ.
J. Org. Chem.
1985,
50:
146
2b Trost BM.
Bonk PJ.
J. Am. Chem. Soc.
1985,
107:
1778
2c Yamamoto Y.
Nishii S.
Maruyama K.
J. Org. Chem.
1985,
50:
3115
2d Bellucci C.
Cozzi PG.
Umani-Ronchi A.
Tetrahedron Lett.
1995,
36:
7289
2e Kobayashi S.
Nagayama S.
J. Am. Chem. Soc.
1997,
119:
10049
2f Kobayashi S.
Iwamoto S.
Nagayama S.
Synlett
1997,
1099
2g Andrade CKZ.
Oliveira GR.
Tetrahedron Lett.
2002,
43:
1935
2h Andrade CKZ.
Azevedo NR.
Oliveira GR.
Synthesis
2002,
928
3 Nakamura H.
Iwama H.
Yamamoto Y.
J. Am. Chem. Soc.
1996,
118:
6641
4 Kobayashi S.
Araki M.
Yasuda M.
Tetrahedron Lett.
1995,
36:
5773
5a Kobayashi S.
Busujima T.
Nagayama S.
Chem. Commun.
1998,
19
5b Aspinall HC.
Greeves N.
McIver EG.
Tetrahedron Lett.
1998,
39:
9283
5c Manabe K.
Mori Y.
Kobayashi S.
Tetrahedron
2001,
57:
2537
5d Yadav JS.
Reddy BVS.
Reddy PSR.
Shesha Rao M.
Tetrahedron Lett.
2002,
43:
6245
5e Choudary BM.
Chidara S.
Sekhar CCV.
Synlett
2002,
1694
5f Aspinall HC.
Bissett JSB.
Greeves N.
Levin D.
Tetrahedron Lett.
2002,
43:
323
5g Yadav JS.
Reddy BVS.
Raju AK.
Gnaneshwar D.
Adv. Synth. Catal.
2002,
344:
938
5h Yadav JS.
Reddy BVS.
Raju AK.
Synthesis
2003,
883
5i Shibata I.
Nose K.
Sakamoto K.
Yasuda M.
Baba A.
J. Org. Chem.
2004,
69:
2185
6a Li G.-l.
Zhao G.
J. Org. Chem.
2005,
70:
4272
6b Li G.-l.
Zhao G.
Synlett
2005,
2540
7a Li G.-l.
Zhao G.
Org. Lett.
2006,
8:
633
7b Li G.-l.
Zhao G.
Org. Lett.
2006,
8:
1011
8 Bloch R.
Chem. Rev.
1998,
98:
1407
9 Benzaldehyde (16 mg, 0.15 mmol), aniline (14 mg, 0.15 mmol), and maleic acid (18 mg, 0.15 mmol) were added successively to CD3 CN (0.5 mL), and the mixture was monitored by 1 H NMR. It was obvious that the corresponding iminium salt was produced and aniline had disappeared completely.
10 Jones WJ.
Davies WZ.
Bowden ST.
Edwards C.
Daris VV.
Thomas LH.
J. Chem. Soc.
1947,
1446
11 Hoffmann RW.
Feussner G.
Zeiss H.-J.
Schulz S.
J. Organomet. Chem.
1980,
18:
321
12 Gyldenfeldt F.
Marton D.
Tagliavini G.
Organometallics
1994,
13:
906
13 Micalizio GC.
Pinchuk AN.
Roush WR.
J. Org. Chem.
2000,
65:
8730
14 Pratt AJ.
Thomas EJ.
J. Chem. Soc., Perkin Trans. 1
1989,
1521
