Abstract
HCl-catalyzed Mannich reaction of cyclic ketone, aromatic aldehyde, and aromatic amine proceeded smoothly in water in the presence of SDS to afford the corresponding β-amino ketone with high anti selectivity.
Key words
Mannich reactions - Brønsted acid - water - amines - surfactant
References
1a
Li C.-J.
Chem. Rev.
1993,
93:
2023
1b
Li C.-J.
Chan T.-H.
Organic Reactions in Aqueous Media
John Wiley;
New York:
1997.
1c
Lubineau A.
Augé J.
Queneau Y.
Synthesis
1994,
741
1d
Li C.-J.
Tetrahedron
1996,
52:
5643
1e
Organic Reactions in Water
Grieco P.
Blackie Academic and Professional;
London:
1998.
1f
Modern Solvents in Organic Synthesis, In Topics in Current Chemistry
Vol. 206:
Knochel P.
Houk KN.
Kessler H.
Springer Verlag;
Berlin:
1999.
1g
Lindstrom UM.
Chem. Rev.
2002,
102:
2751
2
Ribe S.
Wipf P.
Chem. Commun.
2001,
299
3a
Kleinman EF. In Comprehensive Organic Synthesis
Vol. 2:
Trost BM.
Fleming I.
Pergamon Press;
Oxford:
1991.
p.893
3b
Arend M.
Westermann B.
Risch N.
Angew. Chem. Int. Ed.
1998,
37:
1045
3c
Kobayashi S.
Ishitani H.
Chem. Rev.
1999,
99:
1069
4a
Akiyama T.
Takaya J.
Kagoshima H.
Synlett
1999,
1045
4b
Akiyama T.
Takaya J.
Kagoshima H.
Tetrahedron Lett.
1999,
40:
7831
5a
Akiyama T.
Takaya J.
Kagoshima H.
Synlett
1999,
1426
5b
Akiyama T.
Takaya J.
Kagoshima H.
Adv. Synth. Catal.
2002,
344:
338
5c
Akiyama T.
Itoh J.
Fuchibe K.
Synlett
2002,
1269
6
Akiyama T.
Takaya J.
Kagoshima H.
Tetrahedron Lett.
2001,
42:
4025
Recent examples in H2 O-SDS-system, see:
7a
Manabe K.
Mori Y.
Kobayashi S.
Synlett
1999,
1401
7b
Yonehara K.
Ohe K.
Uemura S.
J. Org. Chem.
1999,
64:
9381
7c
Lautens M.
Roy A.
Fukuoka K.
Fagnou K.
Martin-Matute B.
J. Am. Chem. Soc.
2001,
123:
5358
Recent examples of direct Mannich reaction, see:
8a
List B.
Pojarliev P.
Biller WT.
Martin HJ.
J. Am. Chem. Soc.
2002,
124:
827
8b
Trost BM.
Terrell LR.
J. Am. Chem. Soc.
2003,
125:
338
8c
Matsunaga S.
Kumagai N.
Harada S.
Shibasaki M.
J. Am. Chem. Soc.
2003,
125:
4712
8d
Uraguchi D.
Terada M.
J. Am. Chem. Soc.
2004,
126:
5356
HCl-catalyzed Mannich reactions of imine and cyclic ketones, see:
9a
Blatt AH.
Gross N.
J. Org. Chem.
1964,
29:
3306
9b
Yi L.
Zou J.
Lei H.
Lin X.
Zhang M.
Org. Prep. Proced. Int.
1991,
23:
67
Brønsted acid-catalyzed Mannich reaction in water, see:
10a
Manabe K.
Kobayashi S.
Org. Lett.
1999,
1:
1965
10b
Manabe K.
Mori Y.
Kobayashi S.
Tetrahedron
2001,
57:
2537
11 Although Brønsted acid-catalyzed Mannich reactions have been reported,
[9 ]
[10 ]
high stereoselectivity has not been observed.
12 We have not observed the diaminoalkylation product.
13 Other acyclic ketones such as 2-butanone and propiophenone did not give the Mannich adduct.