Abstract
The addition of acyl anion equivalents to aliphatic aldehydes
(crossed-acyloin reaction) has been developed. Cesium fluoride with
isopropanol as solvent promotes the addition of O -silyl thiazolium
carbinols to various aliphatic aldehydes in moderate to good yields.
These reactions represent a general procedure for the selective
coupling of aliphatic aldehydes by an acyl anion reaction which
have been problematic until now.
Key words
acyloin reaction - carbinols - cesium fluoride - acyl anions - thiazolium
References and Notes
1
Seebach D.
Angew.
Chem., Int. Ed. Engl.
1979,
18:
239
2
Grobel BT.
Seebach D.
Synthesis
1977,
357
3
Breslow R.
J.
Am. Chem. Soc.
1958,
79:
3719
4
Breslow R.
Schmuck C.
Tetrahedron Lett.
1996,
37:
8241
5
Chen YT.
Barletta GL.
Haghjoo K.
Cheng JT.
Jordan F.
J.
Org. Chem.
1994,
59:
7714
6
Hassner A.
Lokanatha Rai KM. In
Comprehensive Organic Synthesis
Vol.
1:
Trost BM.
Fleming I.
Pergamon Press;
Oxford:
1991.
p.541-577
7
White MJ.
Leeper FJ.
J. Org. Chem.
2001,
66:
5124
8
Harrington PE.
Tius MA.
Org. Lett.
1999,
1:
649
9
Hempenius MA.
Langeveld-Voss BMW.
van
Haare JAEH.
Janssen RAJ.
Sheiko SS.
Spatz JP.
Moller M.
Meijer EW.
J. Am. Chem. Soc.
1998,
120:
2798
10
Stetter H.
Angew.
Chem., Int. Ed. Engl.
1976,
15:
639
11
Stetter H.
Kuhlmann H.
Synthesis
1975,
379
12
Stetter H.
Kuhlmann H.
Chem. Ber.
1976,
109:
2890
13
Enders D.
Niemeier O.
Synlett
2004,
2111
14
Takikawa H.
Hachisu Y.
Bode JW.
Suzuki K.
Angew. Chem. Int. Ed.
2006,
45:
3492
15
Kramme R.
Martin HD.
Mayer B.
Weimann R.
Angew. Chem., Int. Ed. Engl.
1986,
25:
1116
16
Kurniadi TH.
Rhlid RB.
Juillerat MA.
Gefflaut T.
Bolte J.
Berger RG.
Tetrahedron
2003,
59:
6109
17
Kurniadi TH.
Rhlid RB.
Juillerat MA.
Schuler M.
Berger RG.
Tetrahedron: Asymmetry
2003,
14:
363
18
Matsumoto T.
Ohishi M.
Inoue S.
J.
Org. Chem.
1985,
50:
603
19
Stetter H.
Dambkes G.
Synthesis
1977,
403
20
Linghu X.
Bauch CC.
Johnson JS.
J. Am. Chem. Soc.
2005,
1833
21
Albright JD.
Tetrahedron
1983,
39:
3207
22
Hunig S.
Marschner C.
Chem. Ber.
1989,
122:
1329
23
Seebach D.
Synthesis
1969,
17
24
Smith AB.
Adams CM.
Acc. Chem. Res.
2004,
37:
365
25
Yus M.
Najera C.
Foubelo F.
Tetrahedron
2003,
59:
6147
26
Smith AB.
Zhu WY.
Shirakami S.
Sfouggatakis C.
Doughty VA.
Bennett CS.
Sakamoto Y.
Org.
Lett.
2003,
5:
761
27
Deng LS.
Huang XP.
Zhao G.
J.
Org. Chem.
2006,
71:
4625
28
Bio MM.
Leighton JL.
J. Org. Chem.
2003,
68:
1693
29
Armstrong A.
Barsanti PA.
Jones LH.
Ahmed G.
J.
Org. Chem.
2000,
65:
7020
30
Fukuda Y.
Okamoto Y.
Tetrahedron
2002,
58:
2513
31
Cousson A.
Legouadec G.
Monneret C.
Florent JC.
J. Chem.
Soc., Chem. Commun.
1993,
388
32
Bharadwaj AR.
Scheidt KA.
Org. Lett.
2004,
6:
2465
33
Mattson AE.
Bharadwaj AR.
Scheidt KA.
J. Am. Chem. Soc.
2004,
126:
2314
34
Mattson AE.
Bharadwaj AR.
Zuhl AM.
Scheidt
KA.
J.
Org. Chem.
2006,
71:
5715
35
Takemiya A.
Hartwig JF.
J. Am. Chem. Soc.
2006,
128:
14800
36
Enders D.
Niemeier O.
Balensiefer T.
Angew.
Chem. Int. Ed.
2006,
45:
1463
37
Enders D.
Niemeier O.
Raabe G.
Synlett
2006,
2431
38
Marion N.
Díez-González S.
Nolan SP.
Angew. Chem. Int. Ed.
2007,
46:
2988
39
Johnson JS.
Angew.
Chem. Int. Ed.
2004,
43:
1326
40
Enders D.
Balensiefer T.
Acc. Chem. Res.
2004,
37:
534
41
Mattson AE.
Zuhl AM.
Reynolds TE.
Scheidt KA.
J.
Am. Chem. Soc.
2006,
128:
4932
42
Mattson AE.
Scheidt KA.
J. Am. Chem. Soc.
2007,
129:
4508
43 The use of aldehydes with benzoyl
and triisopropylsiloxy functionalities was incompatible with this
sequence.
44
Breslow R.
J.
Am. Chem. Soc.
1957,
79:
1762
45
Ugai TTS.
Dokawa S.
J. Pharm.
Chem. Jpn.
1943,
63:
269
46 Gronert S.; Org.
Lett.; 2007 , 9 ,
3065.
47
Bordwell FG.
Satish AV.
J. Am. Chem. Soc.
1991,
113:
985
48
Bordwell FG.
Satish AV.
Jordan F.
Rios CB.
Chung AC.
J.
Am. Chem. Soc.
1990,
112:
792
49
Jordan F.
Kudzin ZH.
Rios CB.
J.
Am. Chem. Soc.
1987,
109:
4415
50
Barletta GL.
Zou Y.
Huskey WP.
Jordan F.
J. Am. Chem. Soc.
1997,
119:
2356
51 The ¹³ C
NMR and IR spectra were not obtained due to decomposition of product
upon purification.