SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 15, 2008, Pages 2271-2274

A catalytic asymmetric Fujiwara-Moritani cyclization

(3) Schiffner, Julia A a Machotta, Axel B a Oestreich, Martin a

a UNIVERSITY OF MÜNSTER (Germany)

Author keywords

Asymmetric catalysis; Cyclizations; Fujiwara Moritani reaction; Oxidative heck reaction; Palladium

Indexed keywords

PALLADIUM;

ARTICLE; CATALYSIS; CYCLIZATION; ENANTIOSELECTIVITY; HECK REACTION; QUANTUM YIELD;

EID: 52949140589 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078271 Document Type: Article

Times cited : (70)

References (64)

1
- 84879868832
- Oestreich, M, Ed, Wiley: Chichester, in press
- The Mizoroki-Heck Reaction; Oestreich, M., Ed.; Wiley: Chichester, 2008, in press.
- (2008) The Mizoroki-Heck Reaction

2
- 33744510833
- Dyker, G, Ed, Wiley-VCH: Weinheim
- (a) Fujiwara, Y.; Kitamura, T. In Handbook of C-H Transformations; Dyker, G., Ed.; Wiley-VCH: Weinheim, 2005, 194.
- (2005) Handbook of C-H Transformations , pp. 194
- Fujiwara, Y.¹ Kitamura, T.²

3
- 33744510833
- Dyker, G, Ed, Wiley-VCH: Weinheim
- (b) Leeuwen, P. W. N. M.; de Vries, J. G. In Handbook of C-H Transformations; Dyker, G., Ed.; Wiley-VCH: Weinheim, 2005, 203.
- (2005) Handbook of C-H Transformations , pp. 203
- Leeuwen, P.W.N.M.¹ de Vries, J.G.²

4
- 52949124765
- Mikami, K, Lautens, M, Eds, Wiley: Hoboken
- (c) Li, Z.; Li, C.-J. In New Frontiers in Asymmetric Catalysis; Mikami, K.; Lautens, M., Eds.; Wiley: Hoboken, 2007, 129.
- (2007) New Frontiers in Asymmetric Catalysis , pp. 129
- Li, Z.¹ Li, C.-J.²

5
- 58249109306
- Ackermann, L, Ed, Wiley-VCH: Weinheim, in press
- (d) Trepohl, V. T.; Oestreich, M. In Modern Arylation Methods; Ackermann, L., Ed.; Wiley-VCH: Weinheim, 2008, in press.
- (2008) Modern Arylation Methods
- Trepohl, V.T.¹ Oestreich, M.²

6
- 0002591690
- (a) Moritani, I.; Fujiwara, Y. Tetrahedron Lett. 1967, 1119.
- (1967) Tetrahedron Lett , pp. 1119
- Moritani, I.¹ Fujiwara, Y.²

7
- 0000875742
- (b) Fujiwara, Y.; Moritani, I.; Danno, S.; Asano, R.; Teranishi, S. J. Am. Chem. Soc. 1969, 91, 7166.
- (1969) J. Am. Chem. Soc , vol.91 , pp. 7166
- Fujiwara, Y.¹ Moritani, I.² Danno, S.³ Asano, R.⁴ Teranishi, S.⁵

8
- 0002924142
- For an early summary, see
- (c) For an early summary, see: Moritani, I.; Fujiwara, Y. Synthesis 1973, 524.
- (1973) Synthesis , pp. 524
- Moritani, I.¹ Fujiwara, Y.²

9
- 33847802782
- Dieck, H. A.; Heck, R. F. J. Org. Chem. 1975, 40, 1083.
- (1975) J. Org. Chem , vol.40 , pp. 1083
- Dieck, H.A.¹ Heck, R.F.²

10
- 0001551026
- (a) Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581.
- (1971) Bull. Chem. Soc. Jpn , vol.44 , pp. 581
- Mizoroki, T.¹ Mori, K.² Ozaki, A.³

11
- 33645896595
- (b) Heck, R. F.; Nolley, J. P., Jr. J. Org. Chem. 1972, 37, 2320.
- (1972) J. Org. Chem , vol.37 , pp. 2320
- Heck, R.F.¹ Nolley Jr., J.P.²

12
- 0034677867
- Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
- (1992) Science , vol.2000 , pp. 287
- Jia, C.¹ Piao, D.² Oyamada, J.³ Lu, W.⁴ Kitamura, T.⁵ Fujiwara, Y.⁶

13
- 0000185795
- t-BuOOH-1,4-benzoquinone: Jia, C.; Lu, W.; Kitamura, T.; Fujiwara, Y. Org. Lett. 1999, 1, 2097.
- (a) t-BuOOH-1,4-benzoquinone: Jia, C.; Lu, W.; Kitamura, T.; Fujiwara, Y. Org. Lett. 1999, 1, 2097.

14
- 0037433243
- 40: Yokota, T.; Tani, M.; Sakaguchi, S.; Ishii, Y. J. Am. Chem. Soc. 2003, 125, 1476.
- 40: Yokota, T.; Tani, M.; Sakaguchi, S.; Ishii, Y. J. Am. Chem. Soc. 2003, 125, 1476.

15
- 0042531833
- 3: Dams, M.; de Vos, D. E.; Celen, S.; Jacobs, P. A. Angew. Chem. Int. Ed. 2003, 42, 3512;
- 3: Dams, M.; de Vos, D. E.; Celen, S.; Jacobs, P. A. Angew. Chem. Int. Ed. 2003, 42, 3512;

16
- 4544315557
- Angew. Chem. 2003, 115, 3636.
- (2003) Angew. Chem , vol.115 , pp. 3636

17
- 18044402758
- 2: Du, X.; Suguro, M.; Hirabayashi, K.; Mori, A.; Nishikata, T.; Hagiwara, N.; Kawata, K.; Okeda, T.; Wang, H. F.; Fugami, K.; Kosugi, M. Org. Lett. 2001, 3, 3313.
- 2: Du, X.; Suguro, M.; Hirabayashi, K.; Mori, A.; Nishikata, T.; Hagiwara, N.; Kawata, K.; Okeda, T.; Wang, H. F.; Fugami, K.; Kosugi, M. Org. Lett. 2001, 3, 3313.

18
- 0141853262
- 2: Jung, Y. C.; Mishra, R. K.; Yoon, C. H.; Jung, K. W. Org. Lett. 2003, 5, 2231.
- 2: Jung, Y. C.; Mishra, R. K.; Yoon, C. H.; Jung, K. W. Org. Lett. 2003, 5, 2231.

19
- 1642520949
- 2: Andappan, M. M. S.; Nilsson, P.; Larhed, M. Chem. Commun. 2004, 218.
- 2: Andappan, M. M. S.; Nilsson, P.; Larhed, M. Chem. Commun. 2004, 218.

20
- 8744308924
- 2: Yoon, C. H.; Yoo, K. S.; Yi, S. W.; Mishra, R. K.; Jung, K. W. Org. Lett. 2004, 6, 4037.
- 2: Yoon, C. H.; Yoo, K. S.; Yi, S. W.; Mishra, R. K.; Jung, K. W. Org. Lett. 2004, 6, 4037.

21
- 3543019095
- 2: Andappan, M. M. S.; Nilsson, P.; von Schenck, H.; Larhed, M. J. Org. Chem. 2004, 69, 5212.
- 2: Andappan, M. M. S.; Nilsson, P.; von Schenck, H.; Larhed, M. J. Org. Chem. 2004, 69, 5212.

22
- 33845572646
- 2 and base-free: Yoo, K. S.; Yoon, C. H.; Jung, K. W. J. Am. Chem. Soc. 2006, 128, 16384.
- 2 and base-free: Yoo, K. S.; Yoon, C. H.; Jung, K. W. J. Am. Chem. Soc. 2006, 128, 16384.

23
- 35348851364
- 2 or 1,4-benzoquinone: Lindh, J.; Enquist, P.-A.; Pilotti, A.; Nilsson, P.; Larhed, M. J. Org. Chem. 2007, 72, 7957.
- 2 or 1,4-benzoquinone: Lindh, J.; Enquist, P.-A.; Pilotti, A.; Nilsson, P.; Larhed, M. J. Org. Chem. 2007, 72, 7957.

24
- 39749102821
- 2- and base-free: Ruan, J.; Li, X.; Saidi, O.; Xiao, J. J. Am. Chem. Soc. 2008, 130, 2424.
- 2- and base-free: Ruan, J.; Li, X.; Saidi, O.; Xiao, J. J. Am. Chem. Soc. 2008, 130, 2424.

25
- 18844405201
- Indoles: a
- Indoles: (a) Grimster, N. P.; Gauntlett, C.; Godfrey, C. R. A.; Gaunt, M. J. Angew. Chem. Int. Ed. 2005, 44, 3125;
- (2005) Angew. Chem. Int. Ed , vol.44 , pp. 3125
- Grimster, N.P.¹ Gauntlett, C.² Godfrey, C.R.A.³ Gaunt, M.J.⁴

26
- 52949114872
- Angew. Chem. 2005, 117, 3185.
- (2005) Angew. Chem , vol.117 , pp. 3185

27
- 17444430801
- (b) Capito, E.; Brown, J. M.; Ricci, A. Chem. Commun. 2005, 1854.
- (2005) Chem. Commun , pp. 1854
- Capito, E.¹ Brown, J.M.² Ricci, A.³

28
- 33644658464
- Pyrroles: Beck, E. M.; Grimster, N. P.; Hatley, R.; Gaunt, M. J. J. Am. Chem. Soc. 2006, 128, 2528.
- (c) Pyrroles: Beck, E. M.; Grimster, N. P.; Hatley, R.; Gaunt, M. J. J. Am. Chem. Soc. 2006, 128, 2528.

29
- 37049117124
- Bingham, A. J.; Dyall, L. K.; Norman, R. O. C.; Thomas, C. B. J. Chem. Soc. C 1970, 1879.
- (1970) J. Chem. Soc. C , pp. 1879
- Bingham, A.J.¹ Dyall, L.K.² Norman, R.O.C.³ Thomas, C.B.⁴

30
- 85008586169
- (a) Furukawa, H.; Yogo, M.; Ito, C.; Wu, T.-S.; Kuoh, C.-S. Chem. Pharm. Bull. 1985, 33, 1320.
- (1985) Chem. Pharm. Bull , vol.33 , pp. 1320
- Furukawa, H.¹ Yogo, M.² Ito, C.³ Wu, T.-S.⁴ Kuoh, C.-S.⁵

31
- 0026093219
- (b) Bittner, S.; Krief, P.; Massil, T. Synthesis 1991, 215.
- (1991) Synthesis , pp. 215
- Bittner, S.¹ Krief, P.² Massil, T.³

32
- 0026028142
- (c) Yogo, M.; Ito, C.; Furukawa, H. Chem. Pharm. Bull. 1991, 39, 328.
- (1991) Chem. Pharm. Bull , vol.39 , pp. 328
- Yogo, M.¹ Ito, C.² Furukawa, H.³

33
- 0028295686
- (d) Knölker, H.-J.; O'Sullivan. N. Tetrahedron Lett. 1994, 35, 1695.
- (1994) Tetrahedron Lett , vol.35 , pp. 1695
- Knölker, H.-J.¹ O'Sullivan, N.²

34
- 33947092471
- (a) Trost, B. M.; Godleski, S. A.; Genêt, J. P. J. Am. Chem. Soc. 1978, 100, 3930.
- (1978) Am. Chem. Soc , vol.100 , pp. 3930
- Trost, B.M.¹ Godleski, S.A.² Genêt, J.P.J.³

35
- 0018380628
- (b) Trost, B. M.; Godleski, S. A.; Belletire, J. L. J. Org. Chem. 1979, 44, 2052.
- (1979) J. Org. Chem , vol.44 , pp. 2052
- Trost, B.M.¹ Godleski, S.A.² Belletire, J.L.³

36
- 0027491837
- (c) Cushing, T. D.; Sanz-Cervera, J. F.; Williams, R. M. J. Am. Chem. Soc. 1993, 115, 9323.
- (1993) J. Am. Chem. Soc , vol.115 , pp. 9323
- Cushing, T.D.¹ Sanz-Cervera, J.F.² Williams, R.M.³

37
- 0030020574
- (d) Cushing, T. D.; Sanz-Cervera, J. F.; Williams, R. M. J. Am. Chem. Soc. 1996, 118, 557.
- (1996) J. Am. Chem. Soc , vol.118 , pp. 557
- Cushing, T.D.¹ Sanz-Cervera, J.F.² Williams, R.M.³

38
- 0141992307
- (e) Williams, R. M.; Cao, J.; Tsujishima, H.; Cox, R. J. J. Am. Chem. Soc. 2003, 125, 12172.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 12172
- Williams, R.M.¹ Cao, J.² Tsujishima, H.³ Cox, R.J.⁴

39
- 0037055075
- (f) Baran, P. S.; Corey, E. J. J. Am. Chem. Soc. 2002, 124, 7904.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 7904
- Baran, P.S.¹ Corey, E.J.²

40
- 0038296199
- (g) Baran, P. S.; Guerrero, C. A.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 5628.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 5628
- Baran, P.S.¹ Guerrero, C.A.² Corey, E.J.³

41
- 3543120754
- (h) Garg, N. K.; Caspi, D. D.; Stoltz, B. M. J. Am. Chem. Soc. 2004, 126, 9552.
- (2004) J. Am. Chem. Soc , vol.126 , pp. 9552
- Garg, N.K.¹ Caspi, D.D.² Stoltz, B.M.³

42
- 17744378379
- (i) Garg, N. K.; Caspi, D. D.; Stoltz, B. M. J. Am. Chem. Soc. 2005, 127, 5970.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 5970
- Garg, N.K.¹ Caspi, D.D.² Stoltz, B.M.³

43
- 0028136733
- 2: Knölker, H.-J.; O'Sullivan, N. Tetrahedron 1994, 50. 10893.
- 2: Knölker, H.-J.; O'Sullivan, N. Tetrahedron 1994, 50. 10893.

44
- 33748597689
- 2: Knölker, H.-J.; Fröhner, W. J. Chem. Soc., Perkin Trans. 1 1998, 173.
- 2: Knölker, H.-J.; Fröhner, W. J. Chem. Soc., Perkin Trans. 1 1998, 173.

45
- 0032487805
- (c) Knölker, H.-J.; Reddy, K. R.; Wagner, A. Tetrahedron Lett. 1998, 39. 8267.
- (1998) Tetrahedron Lett , vol.39 , pp. 8267
- Knölker, H.-J.¹ Reddy, K.R.² Wagner, A.³

46
- 0028893764
- t-BuOOH: Åkermark, B.; Oslob, J. D.; Heuschert, U. Tetrahedron Lett. 1995, 36, 1325.
- (d) t-BuOOH: Åkermark, B.; Oslob, J. D.; Heuschert, U. Tetrahedron Lett. 1995, 36, 1325.

47
- 0032818056
- 2: Hagelin, H.; Oslob, J. D.; Akermark, B. Chem. Eur. J. 1999, 5, 2413.
- 2: Hagelin, H.; Oslob, J. D.; Akermark, B. Chem. Eur. J. 1999, 5, 2413.

48
- 0041624424
- 2: (a) Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2003, 125, 9578.
- 2: (a) Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2003, 125, 9578.

49
- 0141655068
- 1,4-Benzoquinone: (b) Abbiati, G.; Beccalli, E. M.; Broggini, G.; Zoni, C. J. Org. Chem. 2003, 68, 7625.
- 1,4-Benzoquinone: (b) Abbiati, G.; Beccalli, E. M.; Broggini, G.; Zoni, C. J. Org. Chem. 2003, 68, 7625.

50
- 33645927023
- (c) Kong, A.; Han, X.; Lu, X. Org. Lett. 2006, 8, 1339.
- (2006) Org. Lett , vol.8 , pp. 1339
- Kong, A.¹ Han, X.² Lu, X.³

51
- 10044267678
- Oxidative couplings of electron-rich arenes: Zhang, H.; Ferreira, E. M.; Stoltz, B. M. Angew. Chem. Int. Ed. 2004, 43, 6144;
- Oxidative couplings of electron-rich arenes: Zhang, H.; Ferreira, E. M.; Stoltz, B. M. Angew. Chem. Int. Ed. 2004, 43, 6144;

52
- 18844448401
- Angew. Chem. 2004, 116, 6270.
- (2004) Angew. Chem , vol.116 , pp. 6270

53
- 0042379984
- Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945.
- (2003) Chem. Rev , vol.103 , pp. 2945
- Dounay, A.B.¹ Overman, L.E.²

54
- 52949119863
- 3t-Bu as the stoichiometric oxidant): Mikami, K.; Hatano, M.; Terada, M. Chem. Lett. 1999, 55.
- 3t-Bu as the stoichiometric oxidant): Mikami, K.; Hatano, M.; Terada, M. Chem. Lett. 1999, 55.

55
- 27544435182
- Very recently, several approaches to enantioselective oxidative Heck reactions initiated by transmetalation appeared in the literature: (a) Akiyama, K.; Wakabayashi, K.; Mikami, K. Adv. Synth. Catal. 2005, 347, 1569.
- Very recently, several approaches to enantioselective oxidative Heck reactions initiated by transmetalation appeared in the literature: (a) Akiyama, K.; Wakabayashi, K.; Mikami, K. Adv. Synth. Catal. 2005, 347, 1569.

56
- 34248525511
- (b) Penn, L.; Shpruhman, A.; Gelman, D. J. Org. Chem. 2007, 72, 3875.
- (2007) J. Org. Chem , vol.72 , pp. 3875
- Penn, L.¹ Shpruhman, A.² Gelman, D.³

57
- 35048872146
- (c) Yoo, K. S.; Park, C. P.; Yoon, C. H.; Sakaguchi, S.; O'Neill, J.; Jung, K. W. Org. Lett. 2007, 9, 3933.
- (2007) Org. Lett , vol.9 , pp. 3933
- Yoo, K.S.¹ Park, C.P.² Yoon, C.H.³ Sakaguchi, S.⁴ O'Neill, J.⁵ Jung, K.W.⁶

58
- 40749087279
- Akiyama, K.; Mikami, K. Heterocycles 2007, 74, 827.
- (2007) Heterocycles , vol.74 , pp. 827
- Akiyama, K.¹ Mikami, K.²

59
- 0032886391
- Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750.
- (1999) J. Org. Chem , vol.64 , pp. 6750
- Nishimura, T.¹ Onoue, T.² Ohe, K.³ Uemura, S.⁴

60
- 52949152705
- General Procedure for Fujiwara-Moritani Cyclization A flame-dried reaction vessel equipped with a magnetic stir bar is charged with Pd(OAc) 2 (10 mol, as well as the indicated ligand L2-8 (30 mol, and subsequently evacuated and then backfilled with O2 if used as oxidant (three cycles, Otherwise, a solution of the indole and tert- amyl alcohol (0.125 M) and AcOH (0.25 mL per mL of tert-amyl alcohol) are consecutively added. The reaction mixture is maintained at r.t. until a homogeneous tawny solution forms. Then, the oxidant (1.0 equiv, PhCO 3t-Bu or 1,4-benzoquinone, is added, and the resulting reaction mixture is heated at 80°C for 15 h under O2 atmosphere with O2 as the oxidant, After cooling to r.t, the reaction mixture is diluted with MTBE and poured into H2O. The organic layer is separated and washed with sat. aq NaHCO3 and brine. The aqueous phase is extracte
- 2 using cyclohexane-MTBE solvent mixtures.

61
- 84940909672
- Detailed procedures and characterization data will be reported elsewhere. See: (a) L2: Bolm, C.; Weickhardt, K.; Zehnder, M.; Ranff, T. Chem. Ber. 1991, 124, 1173.
- Detailed procedures and characterization data will be reported elsewhere. See: (a) L2: Bolm, C.; Weickhardt, K.; Zehnder, M.; Ranff, T. Chem. Ber. 1991, 124, 1173.

62
- 26244447122
- L3-8 were prepared on the basis of a reported sequence: Oila, M. J.; Tois, J. E.; Koskinen, A. M. P. Tetrahedron 2005, 61, 10748.
- (b) L3-8 were prepared on the basis of a reported sequence: Oila, M. J.; Tois, J. E.; Koskinen, A. M. P. Tetrahedron 2005, 61, 10748.

63
- 52949149279
- Analytical Data for (Z, or (E)-1- Methyl-3-(3-methylpent-3-enyl) indole, Z)-1 or (E)-1]14a (Z)-1 (Z/E > 99:1, 1H NMR (300 MHZ, CDCl3, δ, 1.62(d, J, 6.7 Hz, 3 H, 1.82-1.86 (m, 3 H, 2.48 (br t, J, 8.4 Hz, 2 H, 2.83-2.91 (m, 2 H, 3.78 (s, 3 H, 5.32 (q, J, 6.7 Hz, 1 H, 6.90 (s, 1 H, 7.13-7.20 (m, 1 H, 7.24-7.31 (m, 1 H, 7.31-7.36 (m, 1 H, 7.68 (ddd, J, 7.8, 1.7, 0.9 Hz, 1 H) ppm. 13C NMR (75 MHz, CDCl 3, δ, 13.3, 23.4, 23.5, 32.5, 32.5, 109.1, 115.3, 118.5, 118.9, 119.2, 121.4, 125.8, 127.9, 136.1, 137.0 ppm, E)-1 (E:Z > 99:1, 1H NMR(300 MHz, CDCl3, §, 1.67 (dq, J, 6.7, 1.0 Hz, 3 H, 1.77 (m, 3 H, 2.39-2.49 (m, 2 H, 2.87-2.94 (m, 2 H, 3.78 (s, 3 H, 5.37 (qq, J, 6.8, 1.3 Hz, 1 H, 6.88 (s, 1 H, 7.16 ddd
- 3): δ = 13.4, 15.8, 24.0, 32.5, 40.5, 109.0, 115.3, 118.4, 118.4, 119.0, 121.3, 125.8, 127.9, 135.9, 136.9ppm.

64
- 52949146297
- Analytical Data for, )-3,4-Dimethyl-3-vinyl-1,2,3,4- tetrahydrocyclopenta[b]indole, )-2, α] D20 -17.7 (c 0.565, CHCl3) for 44% ee (Table 3, entry 2, HPLC (Daicel Chiralcel IB column using n-heptane at 15°C, tR= 13.9 min (minor enantiomer) and 16.1 min (major enantiomer, IR (film, 3052 (m, 2926 (s, 2854 (s, 1465 (s) cm-1. 1H NMR (300 MHz, CDCl3, δ, 1.50 (s, 3 H, 2.36 (ddd, J, 13.0, 7.1, 6.1 Hz, 1 H, 2.47-2.58 (m, 1 H, 2.83 (m, 2 H, 3.64 (s, 3 H, 4.98 (dd, J, 17.4, 1.3 Hz, 1 H, 5.06 (dd, J, 10.5, 1.2 Hz, 1 H, 6.09 (dd, J, 17.4, 10.5 Hz, 1 H, 7.09 (ddd, J, 7.5, 7.1 Hz, 1.3 Hz, 1 H, 7.16 (ddd, J, 8.2, 7.0, 1.4 Hz, 1 H, 7.26 (ddd, J, 8.1, 0.9, 0.8 Hz, 1 H, 7.47 (ddd, J, 7.6, 1.3, 0.7 Hz, 1 H) ppm. 13C NMR 75 MHz, CDCl3, δ, 22.5, 23.7, 30.0
- 17N: C, 85.26; H, 8.11; N, 6.63. Found: C, 84.97; H, 8.20; N, 6.54.

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