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Volumn 69, Issue 3, 2004, Pages 997-1000

A Direct Retro-Reformatsky Fragmentation: Formal Ring Enlargement of Cyclic Ketones for Novel and Practical Synthesis of Heterocyclic Enamines

(5) Zhao, Mei Xin a Wang, Mei Xiang a Yu, Chu Yi a Huang, Zhi Tang a Fleet, George W J b

a INSTITUTE OF CHEMISTRY (China)

b UNIVERSITY OF OXFORD (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; HYDROGENATION; SYNTHESIS (CHEMICAL);

FORMAL RING ENLARGEMENT;

KETONES;

ALLOY; AROMATIC HYDROCARBON; COPPER; CYCLIC KETONE; ENAMINE; ESTER; HETEROCYCLIC AMINE; HETEROCYCLIC ENAMINE; KETONE; SODIUM AZIDE; UNCLASSIFIED DRUG; ZINC;

ALKALINITY; ARTICLE; BROMINATION; CATALYSIS; CHEMICAL REACTION; CYCLOADDITION; CYCLOCONDENSATION; HYDROGENATION; POLYMERIZATION; REDUCTION; RETRO REFORMATSKY FRAGMENTATION; RING ENLARGEMENT; STEREOCHEMISTRY; SYNTHESIS; WITTIG REACTION;

EID: 0842285736 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo0351320 Document Type: Article

Times cited : (26)

References (36)

1
- 33751049918
- Enaminones in Heterocyclic Synthesis
- For useful reviews, see: (a) Lue, P.; Greenhill, J. V. Enaminones in Heterocyclic Synthesis. Adv. Heterocycl. Chem. 1997, 67, 209-343.
- (1997) Adv. Heterocycl. Chem. , vol.67 , pp. 209-343
- Lue, P.¹ Greenhill, J.V.²

2
- 0001710323
- Enamines as Synthons in the Synthesis of Heterocycles
- (b) Granik, V. G.; Makarov, V. A. Enamines as Synthons in the Synthesis of Heterocycles. Adv. Heterocycl. Chem. 1999, 72, 283-349.
- (1999) Adv. Heterocycl. Chem. , vol.72 , pp. 283-349
- Granik, V.G.¹ Makarov, V.A.²

3
- 0017575299
- For selected examples, see: (a) Taguchi, H.; Yazawa, H.; Arnett, J. F.; Kishi, Y. Tetrahedron Lett. 1977, 627-630.
- (1977) Tetrahedron Lett. , pp. 627-630
- Taguchi, H.¹ Yazawa, H.² Arnett, J.F.³ Kishi, Y.⁴

4
- 0016313013
- (b) Danishefsky, S.; Etheredge, S. J. J. Org. Chem. 1974, 39, 3430-3432.
- (1974) J. Org. Chem. , vol.39 , pp. 3430-3432
- Danishefsky, S.¹ Etheredge, S.J.²

5
- 0027394922
- (c) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. Org. Chem. 1993, 58, 611-617.
- (1993) J. Org. Chem. , vol.58 , pp. 611-617
- Shen, W.¹ Coburn, C.A.² Bornmann, W.G.³ Danishefsky, S.⁴

6
- 0028113185
- (d) Snyder, L.; Shen, W.; Bornmann, W. G.; Danishefsky, S. J. Org. Chem. 1994, 59, 7033-7037.
- (1994) J. Org. Chem. , vol.59 , pp. 7033-7037
- Snyder, L.¹ Shen, W.² Bornmann, W.G.³ Danishefsky, S.⁴

7
- 0020636640
- (e) Luly, J. R.; Rapoport, H. J. Am. Chem. Soc. 1983, 105, 2859-2866.
- (1983) J. Am. Chem. Soc. , vol.105 , pp. 2859-2866
- Luly, J.R.¹ Rapoport, H.²

8
- 0000442218
- (f) Pinnick, H. W.; Chang, Y.-H. J. Org. Chem. 1978, 43, 4662-4663.
- (1978) J. Org. Chem. , vol.43 , pp. 4662-4663
- Pinnick, H.W.¹ Chang, Y.-H.²

9
- 37049067632
- (g) Buchanan, J. G.; Jigajinni, V. B.; Singh, G.; Wightman, R. T. J. Chem. Soc., Perkin Trans. 1 1987, 2377-2384.
- (1987) J. Chem. Soc., Perkin Trans. 1 , pp. 2377-2384
- Buchanan, J.G.¹ Jigajinni, V.B.² Singh, G.³ Wightman, R.T.⁴

10
- 0028363233
- (h) Paulvannan, K.; Stille, J. R. J. Org. Chem. 1994, 59, 1613-1620.
- (1994) J. Org. Chem. , vol.59 , pp. 1613-1620
- Paulvannan, K.¹ Stille, J.R.²

11
- 0025872902
- (i) Saliou, C.; Fleurant, A.; Celerier, J. P.; Lhommet, G. Tetrahedron Lett. 1991, 32, 3365-3368.
- (1991) Tetrahedron Lett. , vol.32 , pp. 3365-3368
- Saliou, C.¹ Fleurant, A.² Celerier, J.P.³ Lhommet, G.⁴

12
- 0027171786
- (j) Fleurant, A.; Celerier, J. P.; Lhommet, G. Tetrahedron: Asymmetry 1993, 4, 1429-1430.
- (1993) Tetrahedron: Asymmetry , vol.4 , pp. 1429-1430
- Fleurant, A.¹ Celerier, J.P.² Lhommet, G.³

13
- 0030220414
- (k) Thanh, G. V.; Celerier, J. P.; Lhommet, G. Tetrahedron: Asymmetry 1996, 7, 2211-2212.
- (1996) Tetrahedron: Asymmetry , vol.7 , pp. 2211-2212
- Thanh, G.V.¹ Celerier, J.P.² Lhommet, G.³

14
- 0036532581
- For recent examples, see: (a) Cheng, Y.; Yang, H.-B.; Wang, M.-X.; Williams, D. J. Tetrahedron 2002, 58, 2821-2829.
- (2002) Tetrahedron , vol.58 , pp. 2821-2829
- Cheng, Y.¹ Yang, H.-B.² Wang, M.-X.³ Williams, D.J.⁴

15
- 0033579628
- (b) Wang, M.-X.; Miao, W. S.; Cheng, Y.; Huang, Z.-T. Tetrahedron 1999, 55, 14611-14622.
- (1999) Tetrahedron , vol.55 , pp. 14611-14622
- Wang, M.-X.¹ Miao, W.S.² Cheng, Y.³ Huang, Z.-T.⁴

16
- 0842341521
- (c) Liu, Y.; Yu, C.-Y.; Wang, M.-X. ARKIVOC 2003 (ii), 146-154.
- (2003) ARKIVOC , Issue.2 , pp. 146-154
- Liu, Y.¹ Yu, C.-Y.² Wang, M.-X.³

17
- 0032515114
- (d) Folmer, J. J.; Acero, C.; Thai, D. L.; Rapoport, H. J. Org. Chem. 1998, 63, 8170-8182.
- (1998) J. Org. Chem. , vol.63 , pp. 8170-8182
- Folmer, J.J.¹ Acero, C.² Thai, D.L.³ Rapoport, H.⁴

18
- 84987288476
- (a) Roth, M.; Dubs, P.; Götschi, E.; Eschenmoser, A. Helv. Chim. Acta 1971, 54, 710-734.
- (1971) Helv. Chim. Acta , vol.54 , pp. 710-734
- Roth, M.¹ Dubs, P.² Götschi, E.³ Eschenmoser, A.⁴

19
- 0034697704
- and references therein
- (b) Michael, J. P.; Gravestock, D. J. Chem. Soc., Perkin Trans. 1 2000, 1919-1928 and references therein.
- (2000) J. Chem. Soc., Perkin Trans. 1 , pp. 1919-1928
- Michael, J.P.¹ Gravestock, D.²

20
- 33845558898
- Celerier, J.-P.; Deloisy, E.; Lhommet, G.; Maitte, P. J. Org. Chem. 1979, 17, 3089.
- (1979) J. Org. Chem. , vol.17 , pp. 3089
- Celerier, J.-P.¹ Deloisy, E.² Lhommet, G.³ Maitte, P.⁴

21
- 0000441721
- Bertele, E.; Boos, H.; Dinitz, J. D.; Elsinger, F.; Eschenmoser, A.; Felner, I.; Gribi, H. P.; Gshwend, H.; Meyer, E. F.; Pesaro, M.; Scheffold, R. Angew. Chem., Int. Ed. Engl. 1964, 3, 490-496.
- (1964) Angew. Chem., Int. Ed. Engl. , vol.3 , pp. 490-496
- Bertele, E.¹ Boos, H.² Dinitz, J.D.³ Elsinger, F.⁴ Eschenmoser, A.⁵ Felner, I.⁶ Gribi, H.P.⁷ Gshwend, H.⁸ Meyer, E.F.⁹ Pesaro, M.¹⁰ Scheffold, R.¹¹

22
- 0001213432
- Gugelchuk, M. M.; Hart, D. J.; Tsai, Y.-M. J. Org. Chem. 1981, 46, 3671-3675.
- (1981) J. Org. Chem. , vol.46 , pp. 3671-3675
- Gugelchuk, M.M.¹ Hart, D.J.² Tsai, Y.-M.³

23
- 84986482251
- Celerier, J. P.; Richaud, M. G.; Lhommet, G. Synthesis 1983, 195-197.
- (1983) Synthesis , pp. 195-197
- Celerier, J.P.¹ Richaud, M.G.² Lhommet, G.³

24
- 0000800442
- Yamaguchi, M.; Hirao, I. J. Org. Chem. 1985, 50, 1975-1977.
- (1985) J. Org. Chem. , vol.50 , pp. 1975-1977
- Yamaguchi, M.¹ Hirao, I.²

25
- 0033548672
- Lee, H. K.; Kim, J.; Pak, C. S. Tetrahedron Lett. 1999, 40, 2173-2174.
- (1999) Tetrahedron Lett. , vol.40 , pp. 2173-2174
- Lee, H.K.¹ Kim, J.² Pak, C.S.³

26
- 0021095689
- (a) Matsumura, Y.; Fujiwara, J.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 6312-6314.
- (1983) J. Am. Chem. Soc. , vol.105 , pp. 6312-6314
- Matsumura, Y.¹ Fujiwara, J.² Maruoka, K.³ Yamamoto, H.⁴

27
- 0028308762
- (b) Jain, S.; Jain, R.; Singh, J.; Anand, N. Tetrahedron Lett. 1994, 35, 2951-2954.
- (1994) Tetrahedron Lett. , vol.35 , pp. 2951-2954
- Jain, S.¹ Jain, R.² Singh, J.³ Anand, N.⁴

28
- 0021041317
- Hannick, S. M.; Kishi, Y. J. Org. Chem. 1983, 48, 3833-3835.
- (1983) J. Org. Chem. , vol.48 , pp. 3833-3835
- Hannick, S.M.¹ Kishi, Y.²

29
- 0001403455
- Lambert, P. H.; Vaultier, M.; Carrie, R. J. Org. Chem. 1985, 50, 5352-5356.
- (1985) J. Org. Chem. , vol.50 , pp. 5352-5356
- Lambert, P.H.¹ Vaultier, M.² Carrie, R.³

30
- 0000721745
- Michael, J. P.; Hosken, G. D.; Howard, A. S. Tetrahedron 1988, 44, 3025-3036.
- (1988) Tetrahedron , vol.44 , pp. 3025-3036
- Michael, J.P.¹ Hosken, G.D.² Howard, A.S.³

31
- 0037453566
- Wang, M.-X. Liu, Y.; Gao, H.-Y.; Zhang, Y.; Yu, C.-Y.; Huang, Z.-T.; Fleet, G. W. J. J. Org. Chem. 2003, 68, 3281-3286.
- (2003) J. Org. Chem. , vol.68 , pp. 3281-3286
- Wang, M.-X.¹ Liu, Y.² Gao, H.-Y.³ Zhang, Y.⁴ Yu, C.-Y.⁵ Huang, Z.-T.⁶ Fleet, G.W.J.⁷

32
- 0033828562
- Zhang, W.-C.; Li, C.-J. J. Org. Chem. 2000, 65, 5831-5833.
- (2000) J. Org. Chem. , vol.65 , pp. 5831-5833
- Zhang, W.-C.¹ Li, C.-J.²

33
- 33845281940
- Picotin, G.; Miginiac, P. J. Org. Chem. 1987, 52, 4796-4798.
- (1987) J. Org. Chem. , vol.52 , pp. 4796-4798
- Picotin, G.¹ Miginiac, P.²

34
- 33751154925
- and references therein
- Wasserman, H. H.; Baldino, C. M.; Coats, S. J. J. Org. Chem. 1995, 60, 8231-8235 and references therein.
- (1995) J. Org. Chem. , vol.60 , pp. 8231-8235
- Wasserman, H.H.¹ Baldino, C.M.² Coats, S.J.³

35
- 0001139775
- Takaya, H.; Makino, S.; Hayakawa, Y.; Noyori, R. J. Am. Chem. Soc. 1978, 100, 1765-1777.
- (1978) J. Am. Chem. Soc. , vol.100 , pp. 1765-1777
- Takaya, H.¹ Makino, S.² Hayakawa, Y.³ Noyori, R.⁴

36
- 0028130025
- Marchand, P.; Bellassoued, M.-C.; Lhommet, B. G. Synth. Commun. 1994, 24, 2577-2584.
- (1994) Synth. Commun. , vol.24 , pp. 2577-2584
- Marchand, P.¹ Bellassoued, M.-C.² Lhommet, B.G.³

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