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Volumn 352, Issue 18, 2010, Pages 3399-3406

Catalytic asymmetric inverse-electron-demand (IED) [4+2] cycloaddition of salicylaldimines: Preparation of optically active 4-aminobenzopyran derivatives

(6) Bernardi, Luca a Comes Franchini, Mauro a Fochi, Mariafrancesca a Leo, Virginia a Mazzanti, Andrea a Ricci, Alfredo a

a UNIVERSITY OF BOLOGNA (Italy)

Author keywords

asymmetric synthesis; cycloaddition; electron rich alkenes; fused ring systems; organic catalysis

Indexed keywords

EID: 78650353567 PISSN: 16154150 EISSN: 16154169 Source Type: Journal
DOI: 10.1002/adsc.201000608 Document Type: Article

Times cited : (48)

References (64)

1
- 0003143073
- in:, (Ed.: G. P. Ellis), Wiley-Interscience, New York, pp
- E. E. Schweizer, O. Meeder-Nycz, in: Chromenes, Chromanes, Chromones, (Ed.:, G. P. Ellis,), Wiley-Interscience, New York, 1977, pp 11-139
- (1977) Chromenes, Chromanes, Chromones , pp. 11-139
- Schweizer, E.E.¹ Meeder-Nycz, O.²

2
- 0017067458
- W. S. Bowers, T. Ohta, J. S. Cleere, P. A. Marsella, Science 1976, 193, 542-547.
- (1976) Science , vol.193 , pp. 542-547
- Bowers, W.S.¹ Ohta, T.² Cleere, J.S.³ Marsella, P.A.⁴

3
- 84944049928
- in:, Vol. 3, (Eds.: A. R. Katritzky, C. W. Rees), Pergamon, Oxford
- J. Hepworth, in: Comprehensive Heterocyclic Chemistry, Vol. 3, (Eds.:, A. R. Katritzky, C. W. Rees,), Pergamon, Oxford, 1984, pp 737-883.
- (1984) Comprehensive Heterocyclic Chemistry , pp. 737-883
- Hepworth, J.¹

4
- 0034684250
- K. C. Nicolaou, J. A. Pfefferkorn, A. J. Roecker, G.-Q. Cao, S. Barluenga, H. J. Mitchell, J. Am. Chem. Soc. 2000, 122, 9939-9953
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 9939-9953
- Nicolaou, K.C.¹ Pfefferkorn, J.A.² Roecker, A.J.³ Cao, G.-Q.⁴ Barluenga, S.⁵ Mitchell, H.J.⁶

5
- 0025015260
- R. Bergmann, R. Gericke, J. Med. Chem. 1990, 33, 492-504.
- (1990) J. Med. Chem. , vol.33 , pp. 492-504
- Bergmann, R.¹ Gericke, R.²

6
- 8044260833
- G. C. Rovnyak, S. Z. Ahmed, C. Z. Ding, S. Dzwonczyk, F. N. Ferrara, W. G. Humphreys, G. J. Grover, D. Santafianos, K. S. Atwa, A. J. Baird, L. G. McLaughlin, D. E. Normandin, P. G. Sleph, S. C. Traeger, J. Med. Chem. 1997, 40, 24-34
- (1997) J. Med. Chem. , vol.40 , pp. 24-34
- Rovnyak, G.C.¹ Ahmed, S.Z.² Ding, C.Z.³ Dzwonczyk, S.⁴ Ferrara, F.N.⁵ Humphreys, W.G.⁶ Grover, G.J.⁷ Santafianos, D.⁸ Atwa, K.S.⁹ Baird, A.J.¹⁰ McLaughlin, L.G.¹¹ Normandin, D.E.¹² Sleph, P.G.¹³ Traeger, S.C.¹⁴

7
- 0021067533
- J. M. Evans, C. S. Fake, T. C. Hamilton, R. H. Poyser, E. A. Watts, J. Med. Chem. 1983, 26, 1582-1589.
- (1983) J. Med. Chem. , vol.26 , pp. 1582-1589
- Evans, J.M.¹ Fake, C.S.² Hamilton, T.C.³ Poyser, R.H.⁴ Watts, E.A.⁵

8
- 0033601175
- H. Miyazaki, K. Honda, M. Asami, S. Inouse, J. Org. Chem. 1999, 64, 9507-9511
- (1999) J. Org. Chem. , vol.64 , pp. 9507-9511
- Miyazaki, H.¹ Honda, K.² Asami, M.³ Inouse, S.⁴

9
- 33845967538
- R. Senthil Kumar, R. Nagarajan, K. Vijay, P. T. Perumal, Lett. Org. Chem. 2005, 2, 458-460
- (2005) Lett. Org. Chem. , vol.2 , pp. 458-460
- Kumar, R.S.¹ Nagarajan, R.² Vijay, K.³ Perumal, P.T.⁴

10
- 2342492429
- R. Senthil Kumar, R. Nagarajan, P. T. Perumal, Synthesis 2004, 949-959
- (2004) Synthesis , pp. 949-959
- Kumar, R.S.¹ Nagarajan, R.² Perumal, P.T.³

11
- 0035801853
- J. S. Yadav, B. V. S. Reddy, C. Madhuri, G. Sabitha, B. Jagannadh, S. K. Kumar, A. C. Kunwar, Tetrahedron Lett. 2001, 42, 6381-6384
- (2001) Tetrahedron Lett. , vol.42 , pp. 6381-6384
- Yadav, J.S.¹ Reddy, B.V.S.² Madhuri, C.³ Sabitha, G.⁴ Jagannadh, B.⁵ Kumar, S.K.⁶ Kunwar, A.C.⁷

12
- 0037164634
- M. Anniyappan, D. Muralidharan, P. T. Perumal, Tetrahedron 2002, 58, 10301-10307
- (2002) Tetrahedron , vol.58 , pp. 10301-10307
- Anniyappan, M.¹ Muralidharan, D.² Perumal, P.T.³

13
- 13544268632
- J. S. Yadav, B. V. S. Reddy, P. N. Reddy, Chem. Lett. 2004, 1436-1437
- (2004) Chem. Lett. , pp. 1436-1437
- Yadav, J.S.¹ Reddy, B.V.S.² Reddy, P.N.³

14
- 47049125207
- J. Wang, F.-X. Xu, X.-F. Lin, Y.-G. Wang, Tetrahedron Lett. 2008, 49, 5208-5210.
- (2008) Tetrahedron Lett. , vol.49 , pp. 5208-5210
- Wang, J.¹ Xu, F.-X.² Lin, X.-F.³ Wang, Y.-G.⁴

15
- 77950795873
- M. Rueping, M.-Y. Lin, Chem. Eur. J. 2010, 16, 4169-4172.
- (2010) Chem. Eur. J. , vol.16 , pp. 4169-4172
- Rueping, M.¹ Lin, M.-Y.²

16
- 75649099300
- G. Bergonzini, L. Gramigna, A. Mazzanti, M. Fochi, L. Bernardi, A. Ricci, Chem. Commun. 2010, 46, 327-329.
- (2010) Chem. Commun. , vol.46 , pp. 327-329
- Bergonzini, G.¹ Gramigna, L.² Mazzanti, A.³ Fochi, M.⁴ Bernardi, L.⁵ Ricci, A.⁶

17
- 2342521907
- D. Uraguchi M. Terada, J. Am. Chem. Soc. 2004, 126, 5356-5357
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 5356-5357
- Terada, D.U.M.¹

18
- 6044226554
- T. Akiyama, J. Itoh, K. Yokota K. Fuchibe, Angew. Chem. 2004, 116, 1592-1595
- (2004) Angew. Chem. , vol.116 , pp. 1592-1595
- Akiyama, T.¹ Itoh, J.² Fuchibe, K.Y.K.³

19
- 2342570203
- Angew. Chem. Int. Ed. 2004, 43, 1566-1568.
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 1566-1568

20
- 78650394703
- Reviews
- Reviews

21
- 77953261329
- M. Terada, Synthesis 2010, 1929-1982
- (2010) Synthesis , pp. 1929-1982
- Terada, M.¹

22
- 38349189109
- T. Akiyama, Chem. Rev. 2007, 107, 5744-5758
- (2007) Chem. Rev. , vol.107 , pp. 5744-5758
- Akiyama, T.¹

23
- 52049088477
- M. Terada, Chem. Commun. 2008, 4097-4112
- (2008) Chem. Commun. , pp. 4097-4112
- Terada, M.¹

24
- 51049088569
- G. Adair, S. Mukherjee, B. List, Aldrichimica Acta 2008, 41, 31-39
- (2008) Aldrichimica Acta , vol.41 , pp. 31-39
- Adair, G.¹ Mukherjee, S.² List, B.³

25
- 33746322013
- M. S. Taylor E. N. Jacobsen, Angew. Chem. 2006, 118, 1550-1573
- (2006) Angew. Chem. , vol.118 , pp. 1550-1573
- Jacobsen, M.S.T.E.N.¹

26
- 33646468489
- Angew. Chem. Int. Ed. 2006, 45, 1520-1543
- (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 1520-1543

27
- 48649106016
- X. Yu, W. Wang, Chem. Asian J. 2008, 3, 516-532.
- (2008) Chem. Asian J. , vol.3 , pp. 516-532
- Yu, X.¹ Wang, W.²

28
- 30744477746
- R. I. Storer, D. E. Carrera, Y. Ni, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 84-86.
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 84-86
- Storer, R.I.¹ Carrera, D.E.² Ni, Y.³ MacMillan, D.W.C.⁴

29
- 66449100339
- For a review on the assignment of the absolute configurations of organic molecules by TD-DFT see:,; see also
- For a review on the assignment of the absolute configurations of organic molecules by TD-DFT see:, G. Bringmann, T. Bruhn, K. Maksimenka, Y. Hemberger, Eur. J. Org. Chem. 2009, 2717-2727; see also
- (2009) Eur. J. Org. Chem. , pp. 2717-2727
- Bringmann, G.¹ Bruhn, T.² Maksimenka, K.³ Hemberger, Y.⁴

30
- 0037431283
- C. Diedrich, S. Grimme, J. Phys. Chem. A 2003, 107, 2524-2539
- (2003) J. Phys. Chem. A , vol.107 , pp. 2524-2539
- Diedrich, C.¹ Grimme, S.²

31
- 34848827876
- D. Casarini, L. Lunazzi, M. Mancinelli, A. Mazzanti, C. Rosini, J. Org. Chem. 2007, 72, 7667-7676
- (2007) J. Org. Chem. , vol.72 , pp. 7667-7676
- Casarini, D.¹ Lunazzi, L.² Mancinelli, M.³ Mazzanti, A.⁴ Rosini, C.⁵

32
- 34848842727
- A. Goel, F. V. Singh, V. Kumar, M. Reichert, T. A. M Goulder, G. Bringmann, J. Org. Chem. 2007, 72, 7765-7768
- (2007) J. Org. Chem. , vol.72 , pp. 7765-7768
- Goel, A.¹ Singh, F.V.² Kumar, V.³ Reichert, M.⁴ Goulder, T.A.M.⁵ Bringmann, G.⁶

33
- 34247598222
- P. J. Stephens, J. J. Pan, F. J. Devlin, K. Krohn, T. Kurtán, J. Org. Chem. 2007, 72, 3521-3536
- (2007) J. Org. Chem. , vol.72 , pp. 3521-3536
- Stephens, P.J.¹ Pan, J.J.² Devlin, F.J.³ Krohn, K.⁴ Kurtán, T.⁵

34
- 40549086252
- P. J. Stephens, J. J. Pan, F. J. Devlin, J. R. Cheeseman, J. Nat. Prod. 2008, 71, 285-291
- (2008) J. Nat. Prod. , vol.71 , pp. 285-291
- Stephens, P.J.¹ Pan, J.J.² Devlin, F.J.³ Cheeseman, J.R.⁴

35
- 67650480427
- C. Gioia, F. Fini, A. Mazzanti, L. Bernardi, A. Ricci, J. Am. Chem. Soc. 2009, 131, 9614-9615
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 9614-9615
- Gioia, C.¹ Fini, F.² Mazzanti, A.³ Bernardi, L.⁴ Ricci, A.⁵

36
- 70349784950
- G. Bencivenni, L. Y. Wu, B. Giannichi, A. Mazzanti, 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 Giannichi, B.³ Mazzanti, A.⁴ Pesciaioli, F.⁵ Song, M.P.⁶ Bartoli, G.⁷ Melchiorre, P.⁸

37
- 70349784950
- Angew. Chem. Int. Ed. 2009, 48, 7200-7203
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 7200-7203

38
- 77249178205
- G. Pescitelli, S. Di Pietro, C. Cardellicchio, M. Annunziata, M. Capozzi, L. Di Bari, J. Org. Chem. 2010, 75, 1143-1154.
- (2010) J. Org. Chem. , vol.75 , pp. 1143-1154
- Pescitelli, G.¹ Di Pietro, S.² Cardellicchio, C.³ Annunziata, M.⁴ Capozzi, M.⁵ Di Bari, L.⁶

39
- 78650390956
- For the synthesis of enecarbamate 3, see
- For the synthesis of enecarbamate 3, see

40
- 0033550276
- A. Kamatani, L. E. Overman, J. Org. Chem, 1999, 64, 8743-8744
- (1999) J. Org. Chem , vol.64 , pp. 8743-8744
- Kamatani, A.¹ Overman, L.E.²

41
- 0024422301
- G. M. Wieber, L. S. Hegedus, B. Åkermark, E. T. Michalson, J. Org. Chem. 1989, 54, 4649-4653.
- (1989) J. Org. Chem. , vol.54 , pp. 4649-4653
- Wieber, G.M.¹ Hegedus, L.S.² Åkermark, B.³ Michalson, E.T.⁴

42
- 78650314051
- For enecarbamates (enamides) as nucleophiles or dienophiles in phosphoric acid-catalyzed transformations, see
- For enecarbamates (enamides) as nucleophiles or dienophiles in phosphoric acid-catalyzed transformations, see

43
- 33746282355
- M. Terada, K. Machioka, K. Sorimachi, Angew. Chem. 2006, 118, 2312-2315
- (2006) Angew. Chem. , vol.118 , pp. 2312-2315
- Terada, M.¹ MacHioka, K.² Sorimachi, K.³

44
- 33746292951
- Angew. Chem. Int. Ed. 2006, 45, 2254-2257
- (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 2254-2257

45
- 58249096026
- M. Terada, K. Soga, N. Momiyama, Angew. Chem. 2008, 120, 4190-4193
- (2008) Angew. Chem. , vol.120 , pp. 4190-4193
- Terada, M.¹ Soga, K.² Momiyama, N.³

46
- 48249127121
- Angew. Chem. Int. Ed. 2008, 47, 4122-4125
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 4122-4125

47
- 34548259270
- M. Terada, K. Machioka, K. Sorimachi, J. Am. Chem. Soc. 2007, 129, 10336-10337
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 10336-10337
- Terada, M.¹ MacHioka, K.² Sorimachi, K.³

48
- 67749110116
- H. Liu, G. Dagousset, G. Masson, P. Retailleau, J. Zhu, J. Am. Chem. Soc. 2009, 131, 4598-4599
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 4598-4599
- Liu, H.¹ Dagousset, G.² Masson, G.³ Retailleau, P.⁴ Zhu, J.⁵

49
- 72449121324
- for enecarbamates (enamides) as imine surrogates in the presence of phosphoric acids, see
- G. Dagousset, F. Drouet, J. Masson, J. Zhu, Org. Lett. 2009, 11, 5546-5549; for enecarbamates (enamides) as imine surrogates in the presence of phosphoric acids, see
- (2009) Org. Lett. , vol.11 , pp. 5546-5549
- Dagousset, G.¹ Drouet, F.² Masson, J.³ Zhu, J.⁴

50
- 55549105103
- K. Sorimachi, M. Terada, J. Am. Chem. Soc. 2008, 130, 14452-14453
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 14452-14453
- Sorimachi, K.¹ Terada, M.²

51
- 38849129202
- Y.-X. Jia, J. Zhong, S.-F. Zhu, C.-M. Zhang, Q. L. Zhou, Angew. Chem. 2007, 119, 5661-5663
- (2007) Angew. Chem. , vol.119 , pp. 5661-5663
- Jia, Y.-X.¹ Zhong, J.² Zhu, S.-F.³ Zhang, C.-M.⁴ Zhou, Q.L.⁵

52
- 34547155080
- Angew. Chem. Int. Ed. 2007, 46, 5565-5567
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 5565-5567

53
- 52649143143
- in the presence of Lewis acids
- C. Baudequin, A. Zamfir, S. B. Tsogoeva, Chem. Commun. 2008, 4637-4639; in the presence of Lewis acids
- (2008) Chem. Commun. , pp. 4637-4639
- Baudequin, C.¹ Zamfir, A.² Tsogoeva, S.B.³

54
- 33750366006
- S. Kobayashi, T. Gustafsson, Y. Shimizu, H. Kiyohara, R. Matsubara, Org. Lett. 2006, 8, 4923-4925.
- (2006) Org. Lett. , vol.8 , pp. 4923-4925
- Kobayashi, S.¹ Gustafsson, T.² Shimizu, Y.³ Kiyohara, H.⁴ Matsubara, R.⁵

55
- 78650356051
- For the preparation of the 3,3′-dibromo derivative, see
- For the preparation of the 3,3′-dibromo derivative, see

56
- 0034613228
- for phosphoric acid formation, see
- P. Wipf, J. K. Jung, J. Org. Chem. 2000, 65, 6319-6337; for phosphoric acid formation, see
- (2000) J. Org. Chem. , vol.65 , pp. 6319-6337
- Wipf, P.¹ Jung, J.K.²

57
- 61349181405
- W. J. Liu, X. H. Chen and L. Z. Gong, Org. Lett. 2008, 10, 5357-5360.
- (2008) Org. Lett. , vol.10 , pp. 5357-5360
- Liu, W.J.¹ Chen, X.H.² Gong, L.Z.³

58
- 71949088992
- C. Gioia, A. Hauville, L. Bernardi, F. Fini, A. Ricci, Angew. Chem. 2008, 120, 9376-9379
- (2008) Angew. Chem. , vol.120 , pp. 9376-9379
- Gioia, C.¹ Hauville, A.² Bernardi, L.³ Fini, F.⁴ Ricci, A.⁵

59
- 56449130065
- Angew. Chem. Int. Ed. 2008, 47, 9236-9239
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 9236-9239

60
- 75749146675
- C. Gioia, L. Bernardi, A. Ricci, Synthesis 2010, 161-170
- (2010) Synthesis , pp. 161-170
- Gioia, C.¹ Bernardi, L.² Ricci, A.³

61
- 33748339796
- J. Waser, B. Gaspar, H. Nambu, E. M. Carreira, J. Am. Chem. Soc. 2006, 128, 11693-11712
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 11693-11712
- Waser, J.¹ Gaspar, B.² Nambu, H.³ Carreira, E.M.⁴

62
- 77749249065
- X.-F. Wang, J.-R. Chen, Y.-J. Cao, H.-G. Cheng, W.-J. Xiao, Org. Lett. 2010, 12, 1140-1143.
- (2010) Org. Lett. , vol.12 , pp. 1140-1143
- Wang, X.-F.¹ Chen, J.-R.² Cao, Y.-J.³ Cheng, H.-G.⁴ Xiao, W.-J.⁵

63
- 77950271210
- M. Bandini, A. Eichholzer, Angew. Chem. 2009, 121, 9786-9824
- (2009) Angew. Chem. , vol.121 , pp. 9786-9824
- Bandini, M.¹ Eichholzer, A.²

64
- 71949117774
- Angew. Chem. Int. Ed. 2009, 48, 9608-9644.
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 9608-9644

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