References
-
For reviews, see:
-
1a
Reissig H.-U.
In Organic Synthesis Highlights
VCH;
Weinheim:
1991.
p.71
-
1b
Li C.-J.
Chem. Rev.
1993,
93:
2023
-
1c
Li C.-J.
Chan T.-H.
Organic Reactions
in Aqueous Media
John Wiley;
New
York:
1997.
-
1d
Lubineau A.
Aug J.
Queneau Y.
Synthesis
1994,
741
-
1e
Li C.-J.
Tetrahedron
1996,
52:
5643
-
1f
Organic Reactions
in Water
Grieco P.
Blackie
Academic and Professional;
London:
1998.
-
1g In Topics In Current Chemistry, Modern Solvents In Organic Synthesis
Knochel P.
Houk KN.
Kessler H.
Springer
Verlag;
Berlin:
1999.
p.206
- 2 For an example, see: Ribe S.
Wipf P.
Chem. Commun.
2001,
299
-
3a
Kleinman EF.
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
-
Selected examples of Mannich-type
reactions, see:
-
4a
Ojima I.
Inaba S.
Yoshida K.
Tetrahedron
Lett.
1977,
3643
-
4b
Pilli RA.
Russowsky D.
J. Chem.
Soc., Chem. Commun.
1987,
1053
-
4c
Guanti G.
Narisano E.
Banfi L.
Tetrahedron
Lett.
1987,
28:
4331
-
4d
Mukaiyama T.
Kashiwagi K.
Matsui S.
Chem.
Lett.
1989,
1397
-
4e
Mukaiyama T.
Akamatsu H.
Han JS.
Chem.
Lett.
1990,
889
-
4f
Onaka M.
Ohno R.
Yanagiya N.
Izumi Y.
Synlett
1993,
141
-
4g
Ishihara K.
Funahashi K.
Hanaki N.
Miyata M.
Yamamoto H.
Synlett
1994,
963
-
4h
Ishihara K.
Miyata M.
Hattori K.
Tada T.
Yamamoto H.
J.
Am. Chem. Soc.
1994,
116:
10520
-
4i
Miura K.
Nakagawa T.
Hosomi A.
J.
Am. Chem. Soc.
2002,
124:
536
-
Examples of three-component Mannich-type
reactions, see:
-
5a
Kobayashi S.
Ishitani H.
Chem. Commun.
1995,
1379
-
5b
Kobayashi S.
Busujima T.
Nagayama S.
Chem. Commun.
1998,
19
-
5c
Kobayashi S.
Busujima T.
Nagayama S.
Synlett
1999,
545
-
5d
Manabe K.
Mori Y.
Kobayashi S.
Synlett
1999,
1401
-
5e
Loh T.-P.
Wei L.-L.
Tetrahedron Lett.
1998,
39:
323
-
5f
Loh T.-P.
Liung SBKW.
Tan K.-L.
Wei L.-L.
Tetrahedron
2000,
56:
3227
-
5g
Shimizu M.
Itohara S.
Synlett
2000,
1828
-
5h
Shimizu M.
Itohara S.
Hase E.
Chem.
Commun.
2001,
2318
-
Recent examples of asymmetric synthesis,
see:
-
6a
List B.
J.
Am. Chem. Soc.
2000,
122:
9336
-
6b
Juhl K.
Gathergood N.
Jørgensen KA.
Angew. Chem. Int. Ed.
2001,
40:
2995
-
6c
Gastner T.
Ishitani H.
Akiyama R.
Kobayashi S.
Angew. Chem. Int. Ed.
2001,
40:
1896
-
6d
Xue S.
Yu S.
Deng Y.
Wulff WD.
Angew. Chem. Int. Ed.
2001,
41:
2271 ; see also references cited therein
-
7a
Akiyama T.
Takaya J.
Kagoshima H.
Chem. Lett.
1999,
947
-
7b
Akiyama T.
Takaya J.
Kagoshima H.
Synlett
1999,
1045
-
8a
Akiyama T.
Takaya J.
Kagoshima H.
Synlett
1999,
1426
-
8b
Akiyama T.
Takaya J.
Kagoshima H.
Tetrahedron
Lett.
2001,
42:
4025
-
8c
Akiyama T.
Takaya J.
Kagoshima H.
Adv.
Synth. Catal.
2002,
344:
338
- 9
Akiyama T.
Takaya J.
Kagoshima H.
Tetrahedron
Lett.
1999,
40:
7831
-
Recent examples of synthetic reactions
in water in the co-existence of surfactant, see:
-
11a
Kobayashi S.
Wakabayashi T.
Nagayama S.
Oyamada H.
Tetrahedron Lett.
1997,
38:
4559
-
11b
Manabe K.
Mori Y.
Kobayashi S.
Synlett
1999,
1401
-
11c
Yonehara K.
Ohe K.
Uemura S.
J.
Org. Chem.
1999,
64:
9381
-
11d
Yonehara K.
Hashizume T.
Mori K.
Ohe K.
Uemura S.
J.
Org. Chem.
1999,
64:
5593
-
11e
Manabe K.
Mori Y.
Kobayashi S.
Tetrahedron
2001,
57:
2537
-
11f
Lautens M.
Roy A.
Fukuoka K.
Fagnou K.
Martin-Matute B.
J.
Am. Chem. Soc.
2001,
123:
5358
- 15
Manabe K.
Mori Y.
Wakabayashi T.
Nagayama S.
Kobayashi S.
J.
Am. Chem. Soc.
2000,
122:
7202
10 We optimized the loading of SDS by
use of a silyl enol ether as a substrate in ref.
[8]
12
General Experimental
Procedure for Protocol A (entry 3 of Table 1). Aq solution
of HBF4 (8 µL, 0.0080 mmol, 1.3598 mol/L)
was added to a mixture of N-benzylidene-p-anisidine(1)
(17 mg, 0.0805 mmol), ketene silyl acetal(2a) (48 µL,
0.241 mmol), SDS (8 µL, 0.0080 mmol, 0.10027 mol/L
solution) in H2O (0.5 mL) at r.t. After being stirred
at the temperature for 0.5 h, the reaction was quenched by addition
of sat. NaHCO3 and CH2Cl2. The
aq layer was extracted with CH2Cl2 and the
combined organic layers were washed with brine, dried over anhyd
Na2SO4, and concentrated to dryness. Purification
of the crude mixture by preparative TLC (SiO2, hexane:ethyl
acetate = 10:1, v/v) gave 3a in 94% yield.
13 Because H3PO4 also
worked equally as a Brønsted acid for the present Mannich-type
reaction, presence of the fluoride ion, which might be generated
from HBF4, is not essential for the Mannich-type reaction.
Authors are grateful to a referee for pointing out the issue.
14
General Experimental
Procedure for Protocol B (entry 5 of Table 1). Aq solution
of HBF4 (48 µL, 0.0480 mmol, 1.0 mol/L)
was added to a mixture of N-benzylidene-p-anisidine(1)
(33.6 mg, 0.159 mmol), ketene silyl acetal (2a) (99 µL,
0.477 mmol) in H2O (1.0 mL) at r.t. After being stirred
at the temperature for 0.5 h, the reaction was quenched by addition
of sat. NaHCO3 and CH2Cl2. The
aq layer was extracted with CH2Cl2 and the
combined organic layers were washed with brine, dried over anhyd
Na2SO4, and concentrated to dryness. Purification
of the crude mixture by preparative TLC (SiO2, hexane:ethyl acetate = 10:1,
v/v) gave 3a in 81% yield.