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
For recent reviews, see:
<A NAME="RF07406SS-1A">1a </A>
Davies AG.
Organotin Chemistry
Wiley-VCH;
Weinheim:
2004.
<A NAME="RF07406SS-1B">1b </A>
Hisashi Y.
Koichiro O.
Main Group Metals in Organic Synthesis
Vol. 2:
Wiley-VCH;
Weinheim:
2004.
p.621-720
<A NAME="RF07406SS-1C">1c </A>
Junzo O.
Modern Carbonyl Chemistry
Wiley-VCH;
Weinheim:
2000.
<A NAME="RF07406SS-1D">1d </A>
Marshall JA.
Chem. Rev.
2000,
100:
3163
<A NAME="RF07406SS-1E">1e </A>
Marshall JA.
Chem. Rev.
1996,
96:
31
<A NAME="RF07406SS-1F">1f </A>
Yamamoto Y.
Asao N.
Chem. Rev.
1993,
93:
2207
<A NAME="RF07406SS-1G">1g </A>
Nishigaichi Y.
Takuwa A.
Naruta Y.
Maruyama K.
Tetrahedron
1993,
49:
7395
Using Lewis acids as promoters or catalysts, see:
<A NAME="RF07406SS-2A">2a </A>
Keck GE.
Enholm EJ.
J. Org. Chem.
1985,
50:
146
<A NAME="RF07406SS-2B">2b </A>
Trost BM.
Bonk PJ.
J. Am. Chem. Soc.
1985,
107:
1778
<A NAME="RF07406SS-2C">2c </A>
Yamamoto Y.
Nishii S.
Maruyama K.
J. Org. Chem.
1985,
50:
3115
<A NAME="RF07406SS-2D">2d </A>
Bellucci C.
Cozzi PG.
Umani-Ronchi A.
Tetrahedron Lett.
1995,
36:
7289
<A NAME="RF07406SS-2E">2e </A>
Kobayashi S.
Nagayama S.
J. Am. Chem. Soc.
1997,
119:
10049
<A NAME="RF07406SS-2F">2f </A>
Kobayashi S.
Iwamoto S.
Nagayama S.
Synlett
1997,
1099
<A NAME="RF07406SS-2G">2g </A>
Andrade CKZ.
Oliveira GR.
Tetrahedron Lett.
2002,
43:
1935
<A NAME="RF07406SS-2H">2h </A>
Andrade CKZ.
Azevedo NR.
Oliveira GR.
Synthesis
2002,
928
<A NAME="RF07406SS-3">3 </A>
Nakamura H.
Iwama H.
Yamamoto Y.
J. Am. Chem. Soc.
1996,
118:
6641
<A NAME="RF07406SS-4">4 </A>
Kobayashi S.
Araki M.
Yasuda M.
Tetrahedron Lett.
1995,
36:
5773
<A NAME="RF07406SS-5A">5a </A>
Kobayashi S.
Busujima T.
Nagayama S.
Chem. Commun.
1998,
19
<A NAME="RF07406SS-5B">5b </A>
Aspinall HC.
Greeves N.
McIver EG.
Tetrahedron Lett.
1998,
39:
9283
<A NAME="RF07406SS-5C">5c </A>
Manabe K.
Mori Y.
Kobayashi S.
Tetrahedron
2001,
57:
2537
<A NAME="RF07406SS-5D">5d </A>
Yadav JS.
Reddy BVS.
Reddy PSR.
Shesha Rao M.
Tetrahedron Lett.
2002,
43:
6245
<A NAME="RF07406SS-5E">5e </A>
Choudary BM.
Chidara S.
Sekhar CCV.
Synlett
2002,
1694
<A NAME="RF07406SS-5F">5f </A>
Aspinall HC.
Bissett JSB.
Greeves N.
Levin D.
Tetrahedron Lett.
2002,
43:
323
<A NAME="RF07406SS-5G">5g </A>
Yadav JS.
Reddy BVS.
Raju AK.
Gnaneshwar D.
Adv. Synth. Catal.
2002,
344:
938
<A NAME="RF07406SS-5H">5h </A>
Yadav JS.
Reddy BVS.
Raju AK.
Synthesis
2003,
883
<A NAME="RF07406SS-5I">5i </A>
Shibata I.
Nose K.
Sakamoto K.
Yasuda M.
Baba A.
J. Org. Chem.
2004,
69:
2185
<A NAME="RF07406SS-6A">6a </A>
Li G.-l.
Zhao G.
J. Org. Chem.
2005,
70:
4272
<A NAME="RF07406SS-6B">6b </A>
Li G.-l.
Zhao G.
Synlett
2005,
2540
<A NAME="RF07406SS-7A">7a </A>
Li G.-l.
Zhao G.
Org. Lett.
2006,
8:
633
<A NAME="RF07406SS-7B">7b </A>
Li G.-l.
Zhao G.
Org. Lett.
2006,
8:
1011
<A NAME="RF07406SS-8">8 </A>
Bloch R.
Chem. Rev.
1998,
98:
1407
<A NAME="RF07406SS-9">9 </A>
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.
<A NAME="RF07406SS-10">10 </A>
Jones WJ.
Davies WZ.
Bowden ST.
Edwards C.
Daris VV.
Thomas LH.
J. Chem. Soc.
1947,
1446
<A NAME="RF07406SS-11">11 </A>
Hoffmann RW.
Feussner G.
Zeiss H.-J.
Schulz S.
J. Organomet. Chem.
1980,
18:
321
<A NAME="RF07406SS-12">12 </A>
Gyldenfeldt F.
Marton D.
Tagliavini G.
Organometallics
1994,
13:
906
<A NAME="RF07406SS-13">13 </A>
Micalizio GC.
Pinchuk AN.
Roush WR.
J. Org. Chem.
2000,
65:
8730
<A NAME="RF07406SS-14">14 </A>
Pratt AJ.
Thomas EJ.
J. Chem. Soc., Perkin Trans. 1
1989,
1521