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Volumn 19, Issue 20, 2013, Pages 6213-6216

Catalytic enantioselective formal Hetero-Diels-Alder reactions of enones with isatins to give spirooxindole tetrahydropyranones

(2) Cui, Hai Lei a Tanaka, Fujie a

a OKINAWA INSTITUTE OF SCIENCE AND TECHNOLOGY GRADUATE UNIVERSITY (Japan)

Author keywords

asymmetric catalysis; cycloaddition; heterocycles; organocatalysis; spiro compounds

Indexed keywords

ASYMMETRIC CATALYSIS; DIASTEREO- AND ENANTIOSELECTIVITY; ENANTIOSELECTIVE; HETERO-DIELS-ALDER REACTIONS; HETEROCYCLES; ORGANOCATALYSIS; ORGANOCATALYTIC; SPIRO COMPOUNDS;

CATALYSIS; CATALYSTS; CYCLOADDITION; REACTION KINETICS;

ENANTIOSELECTIVITY;

AMINE; INDOLE DERIVATIVE; ISATIN; KETONE; OXINDOLE; PYRONE DERIVATIVE; SPIRO COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLOADDITION; STEREOISOMERISM; SYNTHESIS;

AMINES; CATALYSIS; CYCLOADDITION REACTION; INDOLES; ISATIN; KETONES; MOLECULAR STRUCTURE; PYRONES; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 84877306893 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.201300595 Document Type: Article

Times cited : (87)

References (40)

1
- 84869188848
- G. S. Singh, Z. Y. Desta, Chem. Rev. 2012, 112, 6104-6155
- (2012) Chem. Rev. , vol.112 , pp. 6104-6155
- Singh, G.S.¹ Desta, Z.Y.²

2
- 84862864632
- N. Ball-Jones, J. J. Basillo, A. K. Franz, Org. Biomol. Chem. 2012, 10, 5165-5181.
- (2012) Org. Biomol. Chem. , vol.10 , pp. 5165-5181
- Ball-Jones, N.¹ Basillo, J.J.² Franz, A.K.³

3
- 70349784950
- G. Bencivenni, L.-Y. Wu, A. Mazzanti, B. Giannichi, F. Pesciaioli, M.-P. Song, G. Bartoli, P. Melchiorre, Angew. Chem. 2009, 121, 7336-7339
- (2009) Angew. Chem. , vol.121 , pp. 7336-7339
- Bencivenni, G.¹ Wu, L.-Y.² Mazzanti, A.³ Giannichi, B.⁴ Pesciaioli, F.⁵ Song, M.-P.⁶ Bartoli, G.⁷ Melchiorre, P.⁸

4
- 70349784950
- Angew. Chem. Int. Ed. 2009, 48, 7200-7203
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 7200-7203

5
- 80052780706
- Y.-B. Lan, H. Zhao, Z.-M. Liu, J.-C. Tao, X.-W. Wang, Org. Lett. 2011, 13, 4866-4869
- (2011) Org. Lett. , vol.13 , pp. 4866-4869
- Lan, Y.-B.¹ Zhao, H.² Liu, Z.-M.³ Tao, J.-C.⁴ Wang, X.-W.⁵

6
- 84868352757
- C. Cassani, P. Melchiorre, Org. Lett. 2012, 14, 5590-5593
- (2012) Org. Lett. , vol.14 , pp. 5590-5593
- Cassani, C.¹ Melchiorre, P.²

7
- 77958461867
- L.-L. Wang, L. Peng, J.-F. Bai, Q.-C. Huang, X.-Y. Xu, K.-X. Wang, Chem. Commun. 2010, 46, 8064-8066
- (2010) Chem. Commun. , vol.46 , pp. 8064-8066
- Wang, L.-L.¹ Peng, L.² Bai, J.-F.³ Huang, Q.-C.⁴ Xu, X.-Y.⁵ Wang, K.-X.⁶

8
- 77749298301
- Q. Wei, L.-Z. Gong, Org. Lett. 2010, 12, 1008-1011.
- (2010) Org. Lett. , vol.12 , pp. 1008-1011
- Wei, Q.¹ Gong, L.-Z.²

9
- 79958821040
- For synthesis of a spirooxindole tetrahydropyranone as a racemic mixture by a multistep route, see:, J. Wang, E. A. Crane, K. A. Scheidt, Org. Lett. 2011, 13, 3086-3089.
- (2011) Org. Lett. , vol.13 , pp. 3086-3089
- Wang, J.¹ Crane, E.A.² Scheidt, K.A.³

10
- 0000442967
- A. G. Dossetter, T. F. Jamison, E. N. Jacobsen, Angew. Chem. 1999, 111, 2549-2552
- (1999) Angew. Chem. , vol.111 , pp. 2549-2552
- Dossetter, A.G.¹ Jamison, T.F.² Jacobsen, E.N.³

11
- 0033549737
- Angew. Chem. Int. Ed. 1999, 38, 2398-2400
- (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 2398-2400

12
- 0037414319
- Y. Yamashita, S. Saito, H. Ishitani, S. Kobayashi, J. Am. Chem. Soc. 2003, 125, 3793-3798
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 3793-3798
- Yamashita, Y.¹ Saito, S.² Ishitani, H.³ Kobayashi, S.⁴

13
- 17444426017
- M. Anada, T. Washio, N. Shimada, S. Kitagaki, M. Nakajima, M. Shiro, S. Hashimoto, Angew. Chem. 2004, 116, 2719-2722
- (2004) Angew. Chem. , vol.116 , pp. 2719-2722
- Anada, M.¹ Washio, T.² Shimada, N.³ Kitagaki, S.⁴ Nakajima, M.⁵ Shiro, M.⁶ Hashimoto, S.⁷

14
- 4544340835
- Angew. Chem. Int. Ed. 2004, 43, 2665-2668
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 2665-2668

15
- 13444265956
- A. K. Unni, N. Takenaka, H. Yamamoto, V. H. Rawal, J. Am. Chem. Soc. 2005, 127, 1336-1337
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 1336-1337
- Unni, A.K.¹ Takenaka, N.² Yamamoto, H.³ Rawal, V.H.⁴

16
- 28844454968
- S. Rajaram, M. S. Sigman, Org. Lett. 2005, 7, 5473-5475
- (2005) Org. Lett. , vol.7 , pp. 5473-5475
- Rajaram, S.¹ Sigman, M.S.²

17
- 70349083415
- N. Momiyama, H. Tabuse, M. Terada, J. Am. Chem. Soc. 2009, 131, 12882-12883
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 12882-12883
- Momiyama, N.¹ Tabuse, H.² Terada, M.³

18
- 84870897063
- J. Guin, C. Rabalakos, B, List, Angew. Chem. 2012, 124, 8989-8993
- (2012) Angew. Chem. , vol.124 , pp. 8989-8993
- Guin, J.¹ Rabalakos, C.² List, B.³

19
- 84865428726
- Angew. Chem. Int. Ed. 2012, 51, 8859-8863.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 8859-8863

20
- 38949102610
- Only a single example of the enamine-based enantioselective hDA reaction of an enone that gave a tetrahydropyranone has been reported (72 h, 45 %, d.r. 77:23, 40 % ee), see:, L.-Q. Lu, X.-N. Xing, X.-F. Wang, Z.-H. Ming, H.-M. Wang, W.-J. Xiao, Tetrahedron Lett. 2008, 49, 1631-1635
- (2008) Tetrahedron Lett. , vol.49 , pp. 1631-1635
- Lu, L.-Q.¹ Xing, X.-N.² Wang, X.-F.³ Ming, Z.-H.⁴ Wang, H.-M.⁵ Xiao, W.-J.⁶

21
- 0037140856
- R. Thayumanavan, B. Dhevalapally, K. Sakthivel, F. Tanaka, C. F. Barbas III., Tetrahedron Lett. 2002, 43, 3817-3820
- (2002) Tetrahedron Lett. , vol.43 , pp. 3817-3820
- Thayumanavan, R.¹ Dhevalapally, B.² Sakthivel, K.³ Tanaka, F.⁴ Barbas III, C.F.⁵

22
- 4544325311
- D. B. Ramachary, N. S, Chowdari, C. F. Barbas III, Angew. Chem. 2003, 115, 4365-4369
- (2003) Angew. Chem. , vol.115 , pp. 4365-4369
- Ramachary, D.B.¹ Chowdari, N.S.² Barbas III, C.F.³

23
- 0141745638
- Angew. Chem. Int. Ed. 2003, 42, 4233-4237
- (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 4233-4237

24
- 75749136172
- L. Y. Wu, G. Bencivenni, M. Mancinelli, A. Mazzanti, G. Bartoli, P. Melchiorre, Angew. Chem. 2009, 121, 7332-7335
- (2009) Angew. Chem. , vol.121 , pp. 7332-7335
- Wu, L.Y.¹ Bencivenni, G.² Mancinelli, M.³ Mazzanti, A.⁴ Bartoli, G.⁵ Melchiorre, P.⁶

25
- 70349786290
- Angew. Chem. Int. Ed. 2009, 48, 7196-7199
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 7196-7199

26
- 84861508945
- Diels-Alder reactions of trienamines
- Diels-Alder reactions of trienamines:, X.-F. Xiong, Q. Zhou, J. Gu, L. Dong, T.-Y. Liu, Y.-C. Chen, Angew. Chem. 2012, 124, 4477-4480
- (2012) Angew. Chem. , vol.124 , pp. 4477-4480
- Xiong, X.-F.¹ Zhou, Q.² Gu, J.³ Dong, L.⁴ Liu, T.-Y.⁵ Chen, Y.-C.⁶

27
- 84860119030
- Angew. Chem. Int. Ed. 2012, 51, 4401-4404
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 4401-4404

28
- 84873355698
- enamine-based aza-Diels-Alder reactions of enones:, and references cited therein
- enamine-based aza-Diels-Alder reactions of enones:, M. P. Lalonde, M. A. McGowan, N. S. Rajapaksa, E. N. Jacobsen, J. Am. Chem. Soc. 2013, 135, 1891-1894, and references cited therein
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 1891-1894
- Lalonde, M.P.¹ McGowan, M.A.² Rajapaksa, N.S.³ Jacobsen, E.N.⁴

29
- 6044262462
- for amine-catalyzed Diels-Alder reactions of enones, in which enamines of enones were not involved to initiate the reactions, see:, N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2004, 116, 1292-1297
- (2004) Angew. Chem. , vol.116 , pp. 1292-1297
- Halland, N.¹ Aburel, P.S.² Jørgensen, K.A.³

30
- 2342614099
- Angew. Chem. Int. Ed. 2004, 43, 1272-1277
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 1272-1277

31
- 84892539825
- J.-W. Xie, W. Chen, R. Li, M. Zeng, W. Du, L. Yue, Y.-C. Chen, Y. Wu, J. Zhu, J. Deng, Angew. Chem. 2007, 119, 5137-5137
- (2007) Angew. Chem. , vol.119 , pp. 5137-5137
- Xie, J.-W.¹ Chen, W.² Li, R.³ Zeng, M.⁴ Du, W.⁵ Yue, L.⁶ Chen, Y.-C.⁷ Wu, Y.⁸ Zhu, J.⁹ Deng, J.¹⁰

32
- 84892539825
- J. Deng, Angew. Chem. 2007, 119, 5137-5137
- (2007) Angew. Chem. , vol.119 , pp. 5137-5137
- Deng, J.¹

33
- 84892557470
- Angew. Chem. Int. Ed. 2007, 46, 3895049-3925049
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 3895049-3925049

34
- 80051716582
- A. Moyano, R. Rios, Chem. Rev. 2011, 111, 4703-4832
- (2011) Chem. Rev. , vol.111 , pp. 4703-4832
- Moyano, A.¹ Rios, R.²

35
- 2442435852
- for enamine-based formal hDA reactions of enones with nitroso compounds, see:, Y. Yamamoto, N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 5962-5963.
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 5962-5963
- Yamamoto, Y.¹ Momiyama, N.² Yamamoto, H.³

36
- 84866359902
- J.-L. Li, T.-Y. Liu, Y.-C. Chen, Acc. Chem. Res. 2012, 45, 1491-1500
- (2012) Acc. Chem. Res. , vol.45 , pp. 1491-1500
- Li, J.-L.¹ Liu, T.-Y.² Chen, Y.-C.³

37
- 77649087999
- C. Grondal, M. Jeanty, D. Enders, Nat. Chem. 2010, 2, 167-178
- (2010) Nat. Chem. , vol.2 , pp. 167-178
- Grondal, C.¹ Jeanty, M.² Enders, D.³

38
- 0041525915
- K. Juhl, A. Jorgensen, Angew. Chem. 2003, 115, 1536-1539
- (2003) Angew. Chem. , vol.115 , pp. 1536-1539
- Juhl, K.¹ Jorgensen, A.²

39
- 0344835672
- Angew. Chem. Int. Ed. 2003, 42, 1498-1501.
- (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 1498-1501

40
- 84877254550
- CCDC-922764 (8; see the Supporting Information) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
- CCDC-922764 (8; see the Supporting Information) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.

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