SCOPUS 정보 검색 플랫폼

Volumn 16, Issue 22, 2010, Pages 6442-6446

Enantioselective synthesis of 3-Azabicyclo[4.1.0]heptenes and 3-Azabicyclo[3.2.0]heptenes by Ir-catalyzed asymmetric allylic amination of N-iosyl propynylamine and Pt-catalyzed cycloisomerization

(4) Xia, Ji Bao a Liu, Wen Bo a Wang, Tian Min a You, Shu Li a

a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY (China)

Author keywords

Amination; Asymmetric catalysis; Cycloisomerization; Enantioselectivity; Iridium

Indexed keywords

ALLYLIC AMINATION; ASYMMETRIC CATALYSIS; CHEMICAL EQUATIONS; CYCLOISOMERIZATION; CYCLOISOMERIZATIONS; ENANTIOSELECTIVE; ENANTIOSELECTIVE SYNTHESIS; HEPTENES; PT-CATALYZED; TETRABUTYLAMMONIUM FLUORIDES; TRIMETHYLSILYL;

AMINES; CATALYSIS; ELECTRON TRANSITIONS; ENANTIOSELECTIVITY; PLATINUM;

IRIDIUM;

AZABICYCLO DERIVATIVE; DRUG DERIVATIVE; HEPTANE; IRIDIUM; N TOSYL PROPYNYLAMINE; N-TOSYL PROPYNYLAMINE; PARGYLINE; PLATINUM;

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

AMINATION; AZABICYCLO COMPOUNDS; CATALYSIS; HEPTANES; IRIDIUM; MOLECULAR STRUCTURE; PARGYLINE; PLATINUM; STEREOISOMERISM;

EID: 77953154393 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.201000467 Document Type: Article

Times cited : (46)

References (63)

1
- 3042642772
- a) T. A. Blizzard, F. DiNinno, J. D. Morgan II, H. Y. Chen, J. Y. Wu, C. Gude, S. Kim, W. Chan, E. T. Birzin, Y. T. Yang, L.-Y. Pai, Z. Zhang, E. C. Hayes, C. A. DaSilva, W. Tang, S. P. Rohrer, J. M. Schaeffer, M. L. Hammond, Bioorg. Med. Chem. Lett. 2004, 14, 3861-3864;
- (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 3861-3864
- Blizzard, T.A.¹ Dininno, F.² Morgan II, J.D.³ Chen, H.Y.⁴ Wu, J.Y.⁵ Gude, C.⁶ Kim, S.⁷ Chan, W.⁸ Birzin, E.T.⁹ Yang, Y.T.¹⁰ Pai, L.-Y.¹¹ Zhang, Z.¹² Hayes, E.C.¹³ Dasilva, C.A.¹⁴ Tang, W.¹⁵ Rohrer, S.P.¹⁶ Schaeffer, J.M.¹⁷ Hammond, M.L.¹⁸

2
- 24344455130
- b) J. M. Rimoldi, S. G. Puppali, E. Isin, P. Bissel, A. Khalil, N. Castagnoli, Jr., Bioorg. Med. Chem. 2005, 13, 5808-5813;
- (2005) Bioorg. Med. Chem. , vol.13 , pp. 5808-5813
- Rimoldi, J.M.¹ Puppali, S.G.² Isin, E.³ Bissel, P.⁴ Khalil, A.⁵ Castagnoli Jr., N.⁶

3
- 33745699185
- c) D. Ellis, K. L. Kuhen, B. Anaclerio, B. Wu, K. Wolff, H. Yin, B. Bursulaya, J. Caldwell, D. Karanewsky, Y. He, Bioorg. Med. Chem. Lett. 2006, 16, 4246-4251;
- (2006) Bioorg. Med. Chem. Lett. , vol.16 , pp. 4246-4251
- Ellis, D.¹ Kuhen, K.L.² Anaclerio, B.³ Wu, B.⁴ Wolff, K.⁵ Yin, H.⁶ Bursulaya, B.⁷ Caldwell, J.⁸ Karanewsky, D.⁹ He, Y.¹⁰

4
- 67650547226
- d) R. Flores, R. Alibés, M. Figueredo, J. Font, Tetrahedron 2009, 65, 6912-6917;
- (2009) Tetrahedron , vol.65 , pp. 6912-6917
- Flores, R.¹ Alibés, R.² Figueredo, M.³ Font, J.⁴

5
- 77953151002
- PCT Int. Appl WO2009109608
- e) M. Bettati, G. Bonanomi, R. Di Fabio, F, Micheli, G, Tedesco, S. Terreni, PCT Int. Appl. WO2009109608, 2009.
- (2009)
- Bettati, M.¹ Bonanomi, G.² Di Fabio, R.³ Micheli, F.⁴ Tedesco, G.⁵ Terreni, S.⁶

6
- 33748441441
- a) T. Matsuda, S. Kadowaki, M. Murakami, Helv. Chim. Acta 2006, 89, 1672-1675;
- (2006) Helv. Chim. Acta , vol.89 , pp. 1672-1675
- Matsuda, T.¹ Kadowaki, S.² Murakami, M.³

7
- 35349012652
- b) M. R. Luzung, P. Mauleón, F. D. Toste, J. Am. Chem. Soc. 2007, 129, 12402-12403;
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 12402-12403
- Luzung, M.R.¹ Mauleón, P.² Toste, F.D.³

8
- 64549112148
- c) F. Zhang, N. S. Simpkins, A. J. Blake, Org. Biomol. Chem. 2009, 7, 1963-1979.
- (2009) Org. Biomol. Chem. , vol.7 , pp. 1963-1979
- Zhang, F.¹ Simpkins, N.S.² Blake, A.J.³

9
- 33845247117
- For recent reviews, see: a) L. Zhang, J. Sun, S. A. Kozmin, Adv. Synth. Catal. 2006, 348, 2271-2296;
- (2006) Adv. Synth. Catal. , vol.348 , pp. 2271-2296
- Zhang, L.¹ Sun, J.² Kozmin, S.A.³

10
- 34548635326
- b) A. Fürstner, P. W. Davies, Angew. Chem. 2007, 119, 3478-3519;
- (2007) Angew. Chem. , vol.119 , pp. 3478-3519
- Fürstner, A.¹ Davies, P.W.²

11
- 34250824768
- Angew. Chem. Int. Ed. 2007, 46, 3410-3449;
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 3410-3449

12
- 51049097913
- c) E. Jiménez-Núñez, A. M. Echavarren, Chem. Rev. 2008, 108, 3326-3350;
- (2008) Chem. Rev. , vol.108 , pp. 3326-3350
- Jiménez-Núñez, E.¹ Echavarren, A.M.²

13
- 54849171800
- d) V. Michelet, P. Y. Toullec, J.-P. Genêt, Angew. Chem. 2008, 120, 4338-4386;
- (2008) Angew. Chem. , vol.120 , pp. 4338-4386
- Michelet, V.¹ Toullec, P.Y.² Genêt, J.-P.³

14
- 46649098072
- Angew. Chem. Int. Ed. 2008, 47, 4268-4315;
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 4268-4315

15
- 58149458880
- e) S. I. Lee, N. Chatani, Chem. Commun. 2009, 371-384;
- (2009) Chem. Commun. , pp. 371-384
- Lee, S.I.¹ Chatani, N.²

16
- 70350496890
- f) A. Fürstner, Chem. Soc. Rev. 2009, 38, 3208-3221.
- (2009) Chem. Soc. Rev. , vol.38 , pp. 3208-3221
- Fürstner, A.¹

17
- 0038081446
- For selected examples, see: a) A. Fürstner, H. Szillat, F. Stelzer, J. Am. Chem. Soc. 2000, 122, 6785-6786;
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 6785-6786
- Fürstner, A.¹ Szillat, H.² Stelzer, F.³

18
- 0035814401
- b) A. Fürstner, F. Stelzer, H. Szillat, J. Am. Chem. Soc. 2001, 123, 11863-11869;
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 11863-11869
- Fürstner, A.¹ Stelzer, F.² Szillat, H.³

19
- 4344653148
- c) C. Nieto-Oberhuber, M.P. Muñoz, E. Buñuel, C. Nevado, D. J. Cardenas, A. M. Echavarren, Angew. Chem. 2004, 116, 2456-2460;
- (2004) Angew. Chem. , vol.116 , pp. 2456-2460
- Nieto-Oberhuber, C.¹ Muñoz, M.P.² Buñuel, E.³ Nevado, C.⁴ Cardenas, D.J.⁵ Echavarren, A.M.⁶

20
- 3242741475
- Angew. Chem. Int. Ed. 2004, 43, 2402-2406;
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 2402-2406

21
- 3543131388
- d) B. P. Peppers, S. T. Diver, J. Am. Chem. Soc. 2004, 126, 9524-9525;
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 9524-9525
- Peppers, B.P.¹ Diver, S.T.²

22
- 20444496467
- e) A. Fürstner, P. W. Davies, T. Gress, J. Am. Chem. Soc. 2005, 127, 8244-8245;
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 8244-8245
- Fürstner, A.¹ Davies, P.W.² Gress, T.³

23
- 33846013923
- f) S. M. Kim, S. I. Lee, Y. K. Chung, Org. Lett. 2006, 8, 5425-5427;
- (2006) Org. Lett. , vol.8 , pp. 5425-5427
- Kim, S.M.¹ Lee, S.I.² Chung, Y.K.³

24
- 34249041501
- g) C. Ferrer, M. Raducan, C. Nevado, C. K. Claverie, A. M. Echavarren, Tetrahedron 2007, 63, 6306-6316;
- (2007) Tetrahedron , vol.63 , pp. 6306-6316
- Ferrer, C.¹ Raducan, M.² Nevado, C.³ Claverie, C.K.⁴ Echavarren, A.M.⁵

25
- 38349080851
- h) C. Nieto-Oberhuber, P. Pérez-Galán, E. Herrero-Gómez, T. Lauterbach, C. Rodríguez, S. López, C. Bour, A. Rosellón, D. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2008, 130, 269-279;
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 269-279
- Nieto-Oberhuber, C.¹ Pérez-Galán, P.² Herrero-Gómez, E.³ Lauterbach, T.⁴ Rodríguez, C.⁵ López, S.⁶ Bour, C.⁷ Rosellón, A.⁸ Cárdenas, D.⁹ Echavarren, A.M.¹⁰

26
- 70350660550
- i) K. Ota, S. I. Lee, J.-M. Tang, M. Takachi, H. Nakai, T. Morimoto, H. Sakurai, K. Kataoka, N. Chatani, J. Am. Chem. Soc. 2009, 131, 15203-15211.
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 15203-15211
- Ota, K.¹ Lee, S.I.² Tang, J.-M.³ Takachi, M.⁴ Nakai, H.⁵ Morimoto, T.⁶ Sakurai, H.⁷ Kataoka, K.⁸ Chatani, N.⁹

27
- 77953151367
- a) T. Shibata, Y. Kobayashi, S. Maekawa, N. Toshida, K. Takagi, Tetrahedron 2005, 61, 901.8-9024;
- (2005) Tetrahedron , vol.61 , pp. 901
- Shibata, T.¹ Kobayashi, Y.² Maekawa, S.³ Toshida, N.⁴ Takagi, K.⁵

28
- 36749059943
- b) D. Brissy, M. Skander, P. Retailleau, A. Marinetti, Organometallics 2007, 26, 5782-5785;
- (2007) Organometallics , vol.26 , pp. 5782-5785
- Brissy, D.¹ Skander, M.² Retailleau, P.³ Marinetti, A.⁴

29
- 61849172307
- c) D. Brissy, M. Skander, P. Retailleau, G. Frison, A. Marinetti, Organometallics 2009, 28, 140-151;
- (2009) Organometallics , vol.28 , pp. 140-151
- Brissy, D.¹ Skander, M.² Retailleau, P.³ Frison, G.⁴ Marinetti, A.⁵

30
- 72849107985
- d) C. M. Chao, D. Beltrami, P. Y. Toullec, V. Michelet, Chem. Commun. 2009, 6988-6990;
- (2009) Chem. Commun. , pp. 6988-6990
- Chao, C.M.¹ Beltrami, D.² Toullec, P.Y.³ Michelet, V.⁴

31
- 66149149009
- e) D. Brissy, M. Skander, H. Jullien, P. Retailleau, A. Marinetti, Org. Lett. 2009, 11, 2137-2139;
- (2009) Org. Lett. , vol.11 , pp. 2137-2139
- Brissy, D.¹ Skander, M.² Jullien, H.³ Retailleau, P.⁴ Marinetti, A.⁵

32
- 77953170579
- f) T. Nishimura, T. Kawamoto, M. Nagaosa, H. Kumamoto, T. Hayashi, Angew. Chem. 2010, 122, 1682-1685;
- (2010) Angew. Chem. , vol.122 , pp. 1682-1685
- Nishimura, T.¹ Kawamoto, T.² Nagaosa, M.³ Kumamoto, H.⁴ Hayashi, T.⁵

33
- 77649147767
- Angew. Chem. Int. Ed. 2010, 49, 1638-1641.
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 1638-1641

34
- 77953175284
- Y. T. Lee, Y. K. Rang, Y. K. Chung, J. Org. Chem. 2009, 74, 7922-7934.
- (2009) J. Org. Chem. , vol.74 , pp. 7922-7934
- Lee, Y.T.¹ Rang, Y.K.² Chung, Y.K.³

35
- 33846935049
- For reviews, see: a) R. Takeuchi, S. Kezuka, Synthesis 2006, 3349-3366;
- (2006) Synthesis , pp. 3349-3366
- Takeuchi, R.¹ Kezuka, S.²

36
- 33846933027
- b) G. Heimchen, A. Dahnz, P. Dübon, M. Schelwies, R. Weihofen, Chem. Commun. 2007, 675-691;
- (2007) Chem. Commun. , pp. 675-691
- Heimchen, G.¹ Dahnz, A.² Dübon, P.³ Schelwies, M.⁴ Weihofen, R.⁵

37
- 84891314830
- (Eds.: L. A. Oro, C. Claver), WileyVCH, Weinheim
- c) G. Heimchen, in Iridium Complexes in Organic Synthesis (Eds.: L. A. Oro, C. Claver), WileyVCH, Weinheim, 2009, pp. 211-250.
- (2009) Iridium Complexes in Organic Synthesis , pp. 211-250
- Heimchen, G.¹

38
- 0037176296
- For selected recent examples, see: a) T. Ohmura, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 15164-15165;
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 15164-15165
- Ohmura, T.¹ Hartwig, J.F.²

39
- 17644389731
- b) K. Tissot-Croset, D. Polet, A. Alexakis, Angew. Chem. 2004, 116, 2480-2482;
- (2004) Angew. Chem. , vol.116 , pp. 2480-2482
- Tissot-Croset, K.¹ Polet, D.² Alexakis, A.³

40
- 3042695125
- Angew. Chem. Int. Ed. 2004, 43, 2426-2428;
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 2426-2428

41
- 33644770199
- c) R. Weihofen, A. Dahnz, O. Tverskoy, G. Heimchen, Chem. Commun. 2005, 3541-3543;
- (2005) Chem. Commun. , pp. 3541-3543
- Weihofen, R.¹ Dahnz, A.² Tverskoy, O.³ Heimchen, G.⁴

42
- 34250840826
- d) R. Weihofen, O. Tverskoy, G. Heimchen, Angew. Chem. 2006, 118, 5673-5676;
- (2006) Angew. Chem. , vol.118 , pp. 5673-5676
- Weihofen, R.¹ Tverskoy, O.² Heimchen, G.³

43
- 33748639706
- Angew. Chem. Int. Ed. 2006, 45, 5546-5549;
- (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 5546-5549

44
- 33846623887
- e) O. V. Singh, H. Han, J. Am. Chem. Soc. 2007, 129, 774-775;
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 774-775
- Singh, O.V.¹ Han, H.²

45
- 35048823480
- f) C. Defieber, M. A. Ariger, P. Moriel, E. M. Carreira, Angew. Chem. 2007, 119, 3200-3204;
- (2007) Angew. Chem. , vol.119 , pp. 3200-3204
- Defieber, C.¹ Ariger, M.A.² Moriel, P.³ Carreira, E.M.⁴

46
- 34250166800
- Angew. Chem. Int. Ed. 2007, 46, 3139-3143;
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 3139-3143

47
- 62949141622
- g) S. Spiess, C. Welter, G. Franck, J.-P. Taquet, G. Heimchen, Angew. Chem. 2008, 120, 7764-7767;
- (2008) Angew. Chem. , vol.120 , pp. 7764-7767
- Spiess, S.¹ Welter, C.² Franck, G.³ Taquet, J.-P.⁴ Heimchen, G.⁵

48
- 54749126182
- Angew. Chem. Int. Ed. 2008, 47, 7652-7655;
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 7652-7655

49
- 67649631306
- h) L. M. Stanley, J. F. Hartwig, J. Am. Chem. Soc. 2009, 131, 8971-8983;
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 8971-8983
- Stanley, L.M.¹ Hartwig, J.F.²

50
- 77953152517
- i) H. He, W.-B. Liu, L.-X. Dai, S.-L. You, Angew. Chem. 2010, 122, 1538-1541;
- (2010) Angew. Chem. , vol.122 , pp. 1538-1541
- He, H.¹ Liu, W.-B.² Dai, L.-X.³ You, S.-L.⁴

51
- 76649133775
- Angew. Chem. Int. Ed. 2010, 49, 1496-1499.
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 1496-1499

52
- 0345306320
- a) C. A. Kiener, C. Shu, C. Incarvito, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 14272-14273;
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 14272-14273
- Kiener, C.A.¹ Shu, C.² Incarvito, C.³ Hartwig, J.F.⁴

53
- 67650564476
- b) S. T. Madrahimov, D. Markovic, J. F. Hartwig, J. Am. Chem. Soc. 2009, 131, 7228-7229;
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 7228-7229
- Madrahimov, S.T.¹ Markovic, D.² Hartwig, J.F.³

54
- 70350475265
- c) S. Spiess, J. A. Raskatov, C. Gnamm, K. Brödner, G. Heimchen, Chem. Eur. J. 2009, 15, 11087-11090.
- (2009) Chem. Eur. J. , vol.15 , pp. 11087-11090
- Spiess, S.¹ Raskatov, J.A.² Gnamm, C.³ Brödner, K.⁴ Heimchen, G.⁵

55
- 77749298192
- Highly selective Ir-catalyzed allylic amination with but-2-ynylamine and enantioselective total synthesis of (-)-α-kainic acid have been carried out by G. Heimchen and co-workers at Organisch-Chemisches-Institut der Ruprecht-Karls-Universität Heidelberg, private communication of Prof. G. Helmchen. Also see: A. Farwick, G. Helmchen, Org. Lett. 2010, 12, 1108-1111.
- (2010) Org. Lett. , vol.12 , pp. 1108-1111
- Farwick, A.¹ Helmchen, G.²

56
- 58249097025
- S. Ueno, J. F. Hartwig, Angew. Chem. 2008, 120, 1954-1957;
- (2008) Angew. Chem. , vol.120 , pp. 1954-1957
- Ueno, S.¹ Hartwig, J.F.²

57
- 41949120990
- Angew. Chem. Int. Ed. 2008, 47, 1928-1931.
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 1928-1931

58
- 54749142526
- a) M. Schelwies, A. L. Dempwolff, F. Rominger, G. Heimchen, Angew. Chem. 2007, 119, 5694-5697;
- (2007) Angew. Chem. , vol.119 , pp. 5694-5697
- Schelwies, M.¹ Dempwolff, A.L.² Rominger, F.³ Heimchen, G.⁴

59
- 34547183880
- Angew. Chem. Int. Ed. 2007, 46, 5598-5601;
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 5598-5601

60
- 70350223587
- b) M. Schelwies, R. Moser, A. L. Dempwolff, F. Rominger, G. Heimchen, Chem. Eur. J. 2009, 15, 10888-10900.
- (2009) Chem. Eur. J. , vol.15 , pp. 10888-10900
- Schelwies, M.¹ Moser, R.² Dempwolff, A.L.³ Rominger, F.⁴ Heimchen, G.⁵

61
- 77953145027
- CCDC-759758 contains the supplementary crystallographic data for (1S,2S,6S)-5da. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.

62
- 77953143545
- CCDC-759757 contains the supplementary crystallographic data for 6 ah. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.

63
- 68949170987
- E. Soriano, J. Marco-Contelles, Acc. Chem. Res. 2009, 42, 1026-1036.
- (2009) Acc. Chem. Res. , vol.42 , pp. 1026-1036
- Soriano, E.¹ Marco-Contelles, J.²

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