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Volumn 9, Issue 26, 2007, Pages 5577-5580

Virtually complete E-selective α,β-unsaturated ester synthesis by Hg(OTf)2-catalyzed hydration of sec-ethoxyalkynyl acetate

(6) Nishizawa, Mugio a Hirakawa, Hiroko a Nakagawa, Yuki a Yamamoto, Hirofumi a Namba, Kosuke a Imagawa, Hiroshi a

a TOKUSHIMA BUNRI UNIVERSITY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ESTER; MERCURY DERIVATIVE; WATER;

ARTICLE; CATALYSIS; CHEMISTRY;

ACETATES; CATALYSIS; ESTERS; MERCURY COMPOUNDS; WATER;

EID: 38349105681 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol702548r Document Type: Article

Times cited : (26)

References (38)

1
- 0001848341
- (a) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863-927.
- (1989) Chem. Rev , vol.89 , pp. 863-927
- Maryanoff, B.E.¹ Reitz, A.B.²

2
- 3242866355
- (b) Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369-379.
- (1996) Acta Chem. Scand , vol.50 , pp. 369-379
- Rein, T.¹ Reiser, O.²

3
- 19544381844
- (c) Dambacher, J.; Zhao, W.; El-Batta, A.; Anness, R.; Jiang, C.; Bergdahl, M. Tetrahedron Lett. 2005, 46, 4473-4477.
- (2005) Tetrahedron Lett , vol.46 , pp. 4473-4477
- Dambacher, J.¹ Zhao, W.² El-Batta, A.³ Anness, R.⁴ Jiang, C.⁵ Bergdahl, M.⁶

4
- 28944451360
- (a) List, B.; Doehring, A.; Fonseca, M. T. H.; Job, A.; Torres, R. R. Tetrahedron 2006, 62, 476-482.
- (2006) Tetrahedron , vol.62 , pp. 476-482
- List, B.¹ Doehring, A.² Fonseca, M.T.H.³ Job, A.⁴ Torres, R.R.⁵

5
- 32644476277
- (b) Sun, W.; Yu, B.; Kuhn, F. E. Tetrahedron Lett. 2006, 47, 1993-1996.
- (2006) Tetrahedron Lett , vol.47 , pp. 1993-1996
- Sun, W.¹ Yu, B.² Kuhn, F.E.³

6
- 33644764723
- (c) Zeitler, K. Org. Lett. 2006, 8, 637-640.
- (2006) Org. Lett , vol.8 , pp. 637-640
- Zeitler, K.¹

7
- 22244478590
- Further references are cited therein
- (d) Concellon, J. M.; Concellon, C.; Mejica, G J. Org. Chem. 2005, 70, 6111-6113. Further references are cited therein.
- (2005) J. Org. Chem , vol.70 , pp. 6111-6113
- Concellon, J.M.¹ Concellon, C.² Mejica, G.³

8
- 84911308831
- (a) Meyer, K. H.; Schuster, K. Chem. Ber. 1922, 55, 819-821.
- (1922) Chem. Ber , vol.55 , pp. 819-821
- Meyer, K.H.¹ Schuster, K.²

9
- 0000964338
- (b) Rupe, H.; Kambli, E. Helv. Chim. Acta 1926, 9, 672.
- (1926) Helv. Chim. Acta , vol.9 , pp. 672
- Rupe, H.¹ Kambli, E.²

10
- 0000894377
- (c) Swaminathan, S.; Narayanan, K. V. Chem. Rev. 1971, 71, 429-438.
- (1971) Chem. Rev , vol.71 , pp. 429-438
- Swaminathan, S.¹ Narayanan, K.V.²

11
- 45549114212
- (d) Chabardes, P. Tetrahedron Lett. 1988, 29, 6253-6256.
- (1988) Tetrahedron Lett , vol.29 , pp. 6253-6256
- Chabardes, P.¹

12
- 0002168063
- (e) Narasaka, K.; Kusama, H.; Hayashi, Y. Chem. Lett. 1991, 1413-1416.
- (1991) Chem. Lett , pp. 1413-1416
- Narasaka, K.¹ Kusama, H.² Hayashi, Y.³

13
- 0026579169
- (f) Narasaka, K.; Kusama, H.; Hayashi, Y. Tetrahedron 1992, 48, 2059-2068.
- (1992) Tetrahedron , vol.48 , pp. 2059-2068
- Narasaka, K.¹ Kusama, H.² Hayashi, Y.³

14
- 67649266051
- (g) Mercier, C.; Chabardes, P. Pure Appl. Chem. 1994, 66, 1509-1518.
- (1994) Pure Appl. Chem , vol.66 , pp. 1509-1518
- Mercier, C.¹ Chabardes, P.²

15
- 0037078485
- (h) Suzuki, T.; Tokunaga, M.; Wakatsuki, Y. Tetrahedron Lett. 2002, 43, 7531-7533.
- (2002) Tetrahedron Lett , vol.43 , pp. 7531-7533
- Suzuki, T.¹ Tokunaga, M.² Wakatsuki, Y.³

16
- 11144277521
- (i) Cadierno, V.; Diez, J.; Garcia-Garrido, S. E.; Gimeno, J. Chem. Commun. 2004, 2716-2717.
- (2004) Chem. Commun , pp. 2716-2717
- Cadierno, V.¹ Diez, J.² Garcia-Garrido, S.E.³ Gimeno, J.⁴

17
- 34250613920
- (j) Yu, M.; Zhang, G.; Zhang, L. Org. Lett. 2007, 9, 2147-2150.
- (2007) Org. Lett , vol.9 , pp. 2147-2150
- Yu, M.¹ Zhang, G.² Zhang, L.³

18
- 32644449371
- Imagawa, H.; Asai, Y.; Takano, H.; Hamagaki, H.; Nishizawa, M. Org. Lett. 2006, 8, 447-450.
- (2006) Org. Lett , vol.8 , pp. 447-450
- Imagawa, H.¹ Asai, Y.² Takano, H.³ Hamagaki, H.⁴ Nishizawa, M.⁵

19
- 0035982912
- (a) Nishizawa, M.; Skwarczynski, M.; Imagawa, H.; Sugihara, T. Chem. Lett. 2002, 12-13.
- (2002) Chem. Lett , pp. 12-13
- Nishizawa, M.¹ Skwarczynski, M.² Imagawa, H.³ Sugihara, T.⁴

20
- 0141852893
- (b) Nishizawa, M.; Yadav, V. K.; Skwarczynski, M.; Takao, H.; Imagawa, H.; Sugihara, T. Org. Lett. 2003, 5, 1609-1611.
- (2003) Org. Lett , vol.5 , pp. 1609-1611
- Nishizawa, M.¹ Yadav, V.K.² Skwarczynski, M.³ Takao, H.⁴ Imagawa, H.⁵ Sugihara, T.⁶

21
- 0347254810
- (c) Nishizawa, M.; Takao, H.; Yadav, V. K.; Imagawa, H.; Sugihara, T. Org. Lett. 2003, 5, 4563-4565.
- (2003) Org. Lett , vol.5 , pp. 4563-4565
- Nishizawa, M.¹ Takao, H.² Yadav, V.K.³ Imagawa, H.⁴ Sugihara, T.⁵

22
- 7044253524
- (d) Imagawa, H.; Kurisaki, T.; Nishizawa, M. Org. Lett. 2004, 6, 3679-3681.
- (2004) Org. Lett , vol.6 , pp. 3679-3681
- Imagawa, H.¹ Kurisaki, T.² Nishizawa, M.³

23
- 13844276158
- (e) Imagawa, H.; Iyenaga, T.; Nishizawa, M. Org. Lett. 2005, 7, 451-453.
- (2005) Org. Lett , vol.7 , pp. 451-453
- Imagawa, H.¹ Iyenaga, T.² Nishizawa, M.³

24
- 15444377872
- (f) Imagawa, H.; Iyenaga, T.; Nishizawa, M. Synlett 2005, 703-705.
- (2005) Synlett , pp. 703-705
- Imagawa, H.¹ Iyenaga, T.² Nishizawa, M.³

25
- 33744518367
- (g) Imagawa, H.; Kinoshita, A.; Fukuyama, T.; Yamamoto, H.; Nishizawa, M. Tetrahedron Lett. 2006, 47, 4729-4731.
- (2006) Tetrahedron Lett , vol.47 , pp. 4729-4731
- Imagawa, H.¹ Kinoshita, A.² Fukuyama, T.³ Yamamoto, H.⁴ Nishizawa, M.⁵

26
- 33749994290
- (h) Yamamoto, H.; Nishiyama, M.; Imagawa, H.; Nishizawa, M. Tetrahedron Lett. 2006, 47, 8369-8373.
- (2006) Tetrahedron Lett , vol.47 , pp. 8369-8373
- Yamamoto, H.¹ Nishiyama, M.² Imagawa, H.³ Nishizawa, M.⁴

27
- 33846807503
- (i) Kurisaki, T.; Naniwa, T.; Yamamoto, H.; Imagawa, H.; Nishizawa, M. Tetrahedron Lett. 2007, 48, 1871-1874.
- (2007) Tetrahedron Lett , vol.48 , pp. 1871-1874
- Kurisaki, T.¹ Naniwa, T.² Yamamoto, H.³ Imagawa, H.⁴ Nishizawa, M.⁵

28
- 34147136585
- (j) Yamamoto, H.; Sasaki, I.; Imagawa, H.; Nishizawa, M. Org. Lett. 2007, 9, 1399-1402.
- (2007) Org. Lett , vol.9 , pp. 1399-1402
- Yamamoto, H.¹ Sasaki, I.² Imagawa, H.³ Nishizawa, M.⁴

29
- 35048815947
- (k) Yamamoto, H.; Pandey, G.; Asai, Y.; Nakano, M.; Kinoshita, A.; Namba, K.; Imagawa, H.; Nishizawa, M. Org. Lett. 2007, 9, 4029-4032.
- (2007) Org. Lett , vol.9 , pp. 4029-4032
- Yamamoto, H.¹ Pandey, G.² Asai, Y.³ Nakano, M.⁴ Kinoshita, A.⁵ Namba, K.⁶ Imagawa, H.⁷ Nishizawa, M.⁸

30
- 33748928795
- (a) Engel, D. A.; Dudley, G. B. Org. Lett. 2006, 8, 4027-4029.
- (2006) Org. Lett , vol.8 , pp. 4027-4029
- Engel, D.A.¹ Dudley, G.B.²

31
- 34247173920
- (b) Lopez, S. S.; Engel, D. A.; Dudley, G. B. Synlett 2007, 949-953.
- (2007) Synlett , pp. 949-953
- Lopez, S.S.¹ Engel, D.A.² Dudley, G.B.³

32
- 18844460949
- Ritter, J. J.; Kalish, J. J. Am. Chem. Soc. 1948, 70, 4045-4048.
- (1948) J. Am. Chem. Soc , vol.70 , pp. 4045-4048
- Ritter, J.J.¹ Kalish, J.²

33
- 33749036284
- Li, Z.; Zhang, J.; Brouwer, C.; Yang, C. G.; Reich, N. W.; He, C. Org. Lett. 2006, 8, 4175-4178.
- (2006) Org. Lett , vol.8 , pp. 4175-4178
- Li, Z.¹ Zhang, J.² Brouwer, C.³ Yang, C.G.⁴ Reich, N.W.⁵ He, C.⁶

34
- 38349096040
- Typical procedure: To a solution of 5 (100 mg, 0.45 mmol) in dichloromethane (4.5 mL) were sequentially added H2O (8.0 μL, 0.45 mmol) and Hg(OTf)2 (0.1 M solution in acetonitrile, 45 μL, 0.0045 mmol) at room temperature, and the mixture was stirred for 20 min at the same temperature. After addition of NaHCO3 solution, organic material was extracted with dichloromethane. Dried and concentrated extract was purified by flash column chromatography on silica gel using hexane-ethyl acetate (15:1) as an eluent to give 6 (74.7 mg, 92, NMR yield 94, as a colorless oil: FTIR (neat) 2928, 2853, 1725, 1650, 1448, 1368, 1274, 1173, 1046, 983 cm -1; 1H NMR (200 MHz, CDCl3) δ 6.92 (dd, J, 15.4, 6.6 Hz, 1H, 5.76 (dd, J, 15.4, 1.6 Hz, 1H, 4.18 (q, J, 7.2 Hz, 1H, 2.13 (m, 1H, 1.60-1.85 (m, 6H, 1.29 (t, J, 7.2 Hz, 1H, 1.01-1.45 (m, 4H, 13C NMR (50 MHz, CDCl3) δ 167.1, 154.2, 118.9
- + 183.1386, found 183.1384.

35
- 38349187074
- This reaction was repeated five times, and 20 was obtained in 55-60% yield
- This reaction was repeated five times, and 20 was obtained in 55-60% yield.

36
- 0042330507
- (a) Chang, M. Y.; Chen, C. Y.; Chen, S. T.; Chang, N. C. Tetrahedron 2003, 59, 7547-7553.
- (2003) Tetrahedron , vol.59 , pp. 7547-7553
- Chang, M.Y.¹ Chen, C.Y.² Chen, S.T.³ Chang, N.C.⁴

37
- 37049083879
- (b) Curran, D. P.; Liu, H. J. Chem. Soc., Perkin Trans. 1 1994, 1377-1393.
- (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 1377-1393
- Curran, D.P.¹ Liu, H.²

38
- 0033552259
- (c) Appella, D. H.; Moritani, Y.; Shintani, R.; Ferreira, E. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9473-9474.
- (1999) J. Am. Chem. Soc , vol.121 , pp. 9473-9474
- Appella, D.H.¹ Moritani, Y.² Shintani, R.³ Ferreira, E.M.⁴ Buchwald, S.L.⁵

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