L.-Z. Dai, M. Shi / Tetrahedron Letters 49 (2008) 6437–6439
6439
Science Foundation of China for the financial support (20472096,
203900502, 20672127, and 20732008).
O
OH
O
R1
H
R2
R1
O
R2
O
O
R3
3
References and notes
J
R3
1. Donnelly, D. M. X.; Meegan, M. J. In Comprehensive Heterocyclic Chemistry;
Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 4, pp
657–712.
2. Recent reviews: (a) Hou, X. L.; Yang, Z.; Wong, H. N. C. In Progress in Heterocyclic
Chemistry; Gribble, G. W., Gilchrist, T. L., Eds.; Pergamon: Oxford, 2002; Vol. 14,
pp 139–179; (b) Cacchi, S. J. Organomet. Chem. 1999, 576, 42; (c) Hou, X. L.;
Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y.; Wong, H. N. C.
Tetrahedron 1998, 54, 1955.
O
O
Au(I)
R1
O
Au(I)
R1
R2
R1
R2
R2
O
O
O
G
R3
H2O
R3
R3
I
H
R
3 = Ar
3. (a) Miller, D. J. Chem. Soc. C 1969, 12; (b) Eichinger, K.; Berbalk, H.; Machat, E.;
Wimmer, J. J. Chem. Res. 1983, 167.
4. Aurrecoechea, J. M.; Solay-Ispizuo, M. Heterocycles 1994, 37, 223.
5. (a) Marson, C. M.; Harper, S.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun.
1994, 1879; (b) Marson, C. M.; Harper, S. Tetrahedron Lett. 1998, 39, 333; (c)
Marson, C. M.; Harper, S. J. Org. Chem. 1998, 63, 9223.
R2
R2
OH
Au(I)
R1
OH
R2
OH
Au(I)
R1
R4
O
Au(I)
R4 = H
3
1
1
2
1
R1
O
R3
O
6. For selected recent reviews on gold-catalyzed reactions, see: (a) Dyker, G.
Angew. Chem., Int. Ed. 2000, 39, 4237; (b) Hashmi, A. S. K. Gold Bull. 2003, 36, 3;
(c) Echavarren, A. M.; Nevado, C. Chem. Soc. Rev. 2004, 33, 431; (d) Arcadi, A.; Di
Giuseppe, S. Curr. Org. Chem. 2004, 8, 795; (e) Hashmi, A. S. K. Angew. Chem., Int.
Ed. 2005, 44, 6990; (f) Hoffmann-Röder, A.; Krause, N. Org. Biomol. Chem. 2005,
3, 387; (g) Ma, S.; Yu, S.; Gu, Z. Angew. Chem., Int. Ed. 2006, 45, 200; (h) Marion,
N.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2750; (i) Gorin, D. J.; Toste, F. D.
Nature 2007, 446, 395; (j) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180; (k)
Jimémez-Núñez, E.; Echavarren, A. M. Chem. Commun. 2007, 333; (l) Fürstner,
A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410.
7. (a) Hashmi, A. S. K.; Sinha, P. Adv. Synth. Catal. 2004, 346, 432; (b) Shi, Z.; He, C.
J. Am. Chem. Soc. 2004, 126, 5964; (c) Pujanauski, B. G.; Prasad, B. A. B.; Sarpong,
R. J. Am. Chem. Soc. 2006, 128, 6786; (d) Dai, L.-Z.; Qi, M.-J.; Shi, Y.-L.; Liu, X.-G.;
Shi, M. Org. Lett. 2007, 9, 3191; (e) Shu, X.-Z.; Liu, X.-Y.; Xiao, H.-Q.; Ji, K.-G.;
Guo, L.-N.; Qi, C.-Z.; Liang, Y.-M. Adv. Synth. Catal. 2007, 349, 2493; (f)
Cordonnier, M.-C.; Blanc, A.; Pale, P. Org. Lett. 2008, 10, 1569; (g) Li, Y.; Tang, P.;
Chen, Y.; Yu, B. J. Org. Chem. 2008, 73, 4323; (h) Dai, L.-Z.; Shi, M. Chem. Eur. J.
2008, 14, 7011.
2
H2O
2 R3
R3
1
B
A
R3 = H, alkyl
H2O
R3
R2
Au(I)
R2
Au(I)
R1
OH
R2
H
O
R1
OH
O
O
O
E
Au(I)
R3
R1
R2
C
R3
D
R3
R1
R1
R3
OH
R2
O
O
8. Gold(III)-catalyzed tandem cyclization of 1-alkynyl-2,3-epoxy alcohols to
spiropyranones was also recently described, see: Shu, X.-Z.; Liu, X.-Y.; Ji,
K.-G.; Xiao, H.-Q.; Liang, Y.-M. Chem. Eur. J. 2008, 14, 5282. Gold(III)-catalyzed
tandem cyclization of 1-oxiranyl-2-alkynyl esters to difurylmethane
derivatives, see: Ji, K.-G.; Shen, Y.-W.; Shu, X.-Z.; Xiao, H.-Q.; Bian, Y.-J.;
Liang, Y.-M. Adv. Synth. Catal. 2008, 350, 1275.
O
O
R2
R2
R3
2
R1
R3
R1
O
F
Scheme 3. Proposed mechanisms for the formation of bisfurans and 1,3-diketones.
9. (a) Teles, J. H.; Brode, S.; Chabanas, M. Angew. Chem., Int. Ed. 1998, 37, 1415; (b)
Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. J. Am. Chem. Soc. 2000, 122, 11553; (c)
Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000,
39, 2285; (d) Staben, S. T.; Kennedy-Smith, J. J.; Toste, F. D. Angew. Chem., Int. Ed.
2004, 45, 5350; (e) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem.
Soc. 2004, 126, 4526; (f) Gorin, D. J.; Davis, R. N.; Toste, F. D. J. Am. Chem. Soc.
2005, 127, 11260; (g) Corkey, B. K.; Toste, F. D. J. Am. Chem. Soc. 2005, 127,
17168.
10. (a) Jiménez-Núñez, E.; Claverie, C. K.; Nieto-Oberhuber, C.; Echavarren, A. M.
Angew. Chem., Int. Ed. 2006, 45, 5452; (b) Zhang, J.; Schmalz, H. G. Angew. Chem.,
Int. Ed. 2006, 45, 6704; (c) Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2005, 127,
6962.
11. Acid-catalyzed dimerization of 2-hydroxymethylfuran, see: (a) Balaban, A. T.;
Bota, A.; Zlota, A. Synthesis 1980, 136; (b) De Sousa Healy, M.; Rest, A. J. J. Chem.
Soc., Perkin Trans. 1 1985, 973; (c) Musau, R. M.; Whiting, A. J. Chem. Soc., Perkin
Trans. 1 1994, 1, 2881.
12. Gold-catalyzed intermolecular nucleophilic addition of the double bond, see:
(a) Yao, X.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 6884; (b) Yang, C.-G.; He, C. J. Am.
Chem. Soc. 2005, 127, 6966; (c) Nyuyen, R.-V.; Yao, X.-Q.; Bohle, D. S.; Li, C.-J.
Org. Lett. 2005, 7, 673; (d) Lin, C.-C.; Teng, T.-M.; Odedra, A.; Liu, R.-S. J. Am.
Chem. Soc. 2007, 129, 3798.
become more difficult. Thus, nucleophilic attack by water is favored
to give oxirane-opening intermediate. On the other hand, in Liang’s
recently published work,8 since C1 (R4 ¼ H) is a quaternary carbon,
the C1–O bond is weaker than C2–O bond in oxonium ion B, the
[1,2]-migration13 of the alkyl group takes place with the assistance
of the hydroxyl group whether R3 is alkyl or aryl group, affording
spiropyranones in good yields.
In summary, we have developed a selective synthetic approach
to bisfurans and 1,3-diketones from 1-alkynyl-2,3-epoxy alcohols
catalyzed by gold(I) at room temperature. Further studies regarding
the mechanistic details and scope of this process are in progress.
Acknowledgments
We thank the Shanghai Municipal Committee of Science and
Technology (04JC14083, 06XD14005), and the National Natural
13. Kirsch, S. F.; Binder, J. T.; Liébert, C.; Menz, H. Angew. Chem., Int. Ed. 2006, 45,
5878.