SCOPUS 정보 검색 플랫폼

Angewandte Chemie - International Edition

Volumn 53, Issue 47, 2014, Pages 12921-12924

Photocycloaddition of 3-alkenyloxy-2-cycloalkenones: Enantioselective lewis acid catalysis and ring expansion

(2) Brimioulle, Richard a Bach, Thorsten a

a TECHNICAL UNIVERSITY OF MUNICH (Germany)

Author keywords

cycloaddition; enantioselectivity; Lewis acids; photochemistry; ring expansion

Indexed keywords

CATALYSIS; CYCLOADDITION; ENANTIOSELECTIVITY; O RINGS; PHOTOCHEMICAL REACTIONS;

DIASTEREOSELECTIVE REDUCTION; HIGH ENANTIOSELECTIVITY; LEWIS ACID; LEWIS ACID CATALYSIS; RING EXPANSION; RING-EXPANSION REACTION; TRICYCLIC PRODUCTS; [2+2] PHOTOCYCLOADDITION;

EXPANSION;

EID: 84941112288 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201407832 Document Type: Article

Times cited : (62)

References (76)

1
- 15644378136
- H. N. C. Wong, M.-Y. Hon, C.-W. Tse, Y.-C. Yip, Chem. Rev. 1989, 89, 165-198;
- (1989) Chem. Rev. , vol.89 , pp. 165-198
- Wong, H.N.C.¹ Hon, M.-Y.² Tse, C.-W.³ Yip, Y.-C.⁴

2
- 0042789931
- P. Dowd, W. Zhang, Chem. Rev. 1993, 93, 2091-2115;
- (1993) Chem. Rev. , vol.93 , pp. 2091-2115
- Dowd, P.¹ Zhang, W.²

3
- 0037509951
- J. C. Namyslo, D. E. Kaufmann, Chem. Rev. 2003, 103, 1485-1537;
- (2003) Chem. Rev. , vol.103 , pp. 1485-1537
- Namyslo, J.C.¹ Kaufmann, D.E.²

4
- 70350512114
- C. A. Carson, M. A. Kerr, Chem. Soc. Rev. 2009, 38, 3051-3060.
- (2009) Chem. Soc. Rev. , vol.38 , pp. 3051-3060
- Carson, C.A.¹ Kerr, M.A.²

5
- 0000330557
- G. Mehta, V. Singh, Chem. Rev. 1999, 99, 881-930;
- (1999) Chem. Rev. , vol.99 , pp. 881-930
- Mehta, G.¹ Singh, V.²

6
- 14844320177
- Beispiele
- J. W. Blunt, B. R. Copp, M. H. G. Munro, P. T. Northcote, M. R. Prinsep, Nat. Prod. Rep. 2005, 22, 15-61; Beispiele:
- (2005) Nat. Prod. Rep. , vol.22 , pp. 15-61
- Blunt, J.W.¹ Copp, B.R.² Munro, M.H.G.³ Northcote, P.T.⁴ Prinsep, M.R.⁵

7
- 0026721571
- N. A. Petasis, M. A. Petane, Tetrahedron 1992, 48, 5757-5821;
- (1992) Tetrahedron , vol.48 , pp. 5757-5821
- Petasis, N.A.¹ Petane, M.A.²

8
- 33646174305
- M. A. Battiste, P. M. Delphrey, D. C. Wright, Chem. Eur. J. 2006, 12, 3438-3447.
- (2006) Chem. Eur. J. , vol.12 , pp. 3438-3447
- Battiste, M.A.¹ Delphrey, P.M.² Wright, D.C.³

9
- 0001239196
- W. Oppolzer, Acc. Chem. Res. 1982, 15, 135-141;
- (1982) Acc. Chem. Res. , vol.15 , pp. 135-141
- Oppolzer, W.¹

10
- 11944265389
- J. D. Winkler, C. M. Bowen, F. Liotta, Chem. Rev. 1995, 95, 2003-2020;
- (1995) Chem. Rev. , vol.95 , pp. 2003-2020
- Winkler, J.D.¹ Bowen, C.M.² Liotta, F.³

11
- 35348986501
- J. Iriondo-Alberdi, M. F. Greaney, Eur. J. Org. Chem. 2007, 4801-4815;
- (2007) Eur. J. Org. Chem. , pp. 4801-4815
- Iriondo-Alberdi, J.¹ Greaney, M.F.²

12
- 42549140767
- N. Hoffmann, Chem. Rev. 2008, 108, 1052-1103;
- (2008) Chem. Rev. , vol.108 , pp. 1052-1103
- Hoffmann, N.¹

13
- 79251579273
- T. Bach, J. P. Hehn, Angew. Chem. Int. Ed. 2011, 50, 1000-1045;
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 1000-1045
- Bach, T.¹ Hehn, J.P.²

14
- 79956121315
- Angew. Chem. 2011, 123, 1032-1077.
- (2011) Angew. Chem. , vol.123 , pp. 1032-1077

15
- 0028949888
- G. L. Lange, C. Gottardo, J. Org. Chem. 1995, 60, 2183-2187;
- (1995) J. Org. Chem. , vol.60 , pp. 2183-2187
- Lange, G.L.¹ Gottardo, C.²

16
- 0030565568
- M. T. Crimmins, S. Huang, L. E. Guise-Zawacki, Tetrahedron Lett. 1996, 37, 6519-6522;
- (1996) Tetrahedron Lett. , vol.37 , pp. 6519-6522
- Crimmins, M.T.¹ Huang, S.² Guise-Zawacki, L.E.³

17
- 0032481587
- M. T. Crimmins, Z. Wang, L. A. McKerlie, J. Am. Chem. Soc. 1998, 120, 1747-1756;
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 1747-1756
- Crimmins, M.T.¹ Wang, Z.² McKerlie, L.A.³

18
- 0032581540
- G. L. Lange, L. Furlan, M. C. MacKinnon, Tetrahedron Lett. 1998, 39, 5489-5492;
- (1998) Tetrahedron Lett. , vol.39 , pp. 5489-5492
- Lange, G.L.¹ Furlan, L.² MacKinnon, M.C.³

19
- 79953201214
- J. P. Hehn, E. Herdtweck, T. Bach, Org. Lett. 2011, 13, 1892-1895.
- (2011) Org. Lett. , vol.13 , pp. 1892-1895
- Hehn, J.P.¹ Herdtweck, E.² Bach, T.³

20
- 0008552089
- H. Hikino, P. de Mayo, J. Am. Chem. Soc. 1964, 86, 3582-3583;
- (1964) J. Am. Chem. Soc. , vol.86 , pp. 3582-3583
- Hikino, H.¹ De Mayo, P.²

21
- 33947292540
- P. de Mayo, Acc. Chem. Res. 1971, 4, 41-47;
- (1971) Acc. Chem. Res. , vol.4 , pp. 41-47
- De Mayo, P.¹

22
- 0000060123
- W. Oppolzer, T. Godel, J. Am. Chem. Soc. 1978, 100, 2583-2584.
- (1978) J. Am. Chem. Soc. , vol.100 , pp. 2583-2584
- Oppolzer, W.¹ Godel, T.²

23
- 0023690543
- J. D. Winkler, C. L. Muller, R. D. Scott, J. Am. Chem. Soc. 1988, 110, 4831-4832;
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 4831-4832
- Winkler, J.D.¹ Muller, C.L.² Scott, R.D.³

24
- 33845184523
- J. D. Winkler, P. M. Hershberger, J. Am. Chem. Soc. 1989, 111, 4852-4856;
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 4852-4856
- Winkler, J.D.¹ Hershberger, P.M.²

25
- 0003695385
- J. D. Winkler, R. D. Scott, P. G. Williard, J. Am. Chem. Soc. 1990, 112, 8971-8975;
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 8971-8975
- Winkler, J.D.¹ Scott, R.D.² Williard, P.G.³

26
- 0032125867
- J. D. Winkler, J. M. Axten, J. Am. Chem. Soc. 1998, 120, 6425-6426.
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 6425-6426
- Winkler, J.D.¹ Axten, J.M.²

27
- 0000107929
- L. M. Tolbert, M. B. Ali, J. Am. Chem. Soc. 1982, 104, 1742-1744;
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 1742-1744
- Tolbert, L.M.¹ Ali, M.B.²

28
- 0000743280
- A. I. Meyers, S. A. Fleming, J. Am. Chem. Soc. 1986, 108, 306-307;
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 306-307
- Meyers, A.I.¹ Fleming, S.A.²

29
- 84985624873
- M. Demuth, A. Palomer, H.-D. Sluma, A. K. Dey, C. Krüger, M.-H. Tsay, Angew. Chem. Int. Ed. Engl. 1986, 25, 1117-1119;
- (1986) Angew. Chem. Int. Ed. Engl. , vol.25 , pp. 1117-1119
- Demuth, M.¹ Palomer, A.² Sluma, H.-D.³ Dey, A.K.⁴ Krüger, C.⁵ Tsay, M.-H.⁶

30
- 0001435632
- Angew. Chem. 1986, 98, 1093-1095;
- (1986) Angew. Chem. , vol.98 , pp. 1093-1095

31
- 0034801436
- C. Chen, V. Chang, X. Cai, E. Duesler, P. S. Mariano, J. Am. Chem. Soc. 2001, 123, 6433-6434;
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 6433-6434
- Chen, C.¹ Chang, V.² Cai, X.³ Duesler, E.⁴ Mariano, P.S.⁵

32
- 1242269266
- H. Saito, T. Mori, T. Wada, Y. Inoue, J. Am. Chem. Soc. 2004, 126, 1900-1906.
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 1900-1906
- Saito, H.¹ Mori, T.² Wada, T.³ Inoue, Y.⁴

33
- 0034601015
- T. Bach, H. Bergmann, K. Harms, Angew. Chem. Int. Ed. 2000, 39, 2302-2304;
- (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 2302-2304
- Bach, T.¹ Bergmann, H.² Harms, K.³

34
- 0000150239
- Angew. Chem. 2000, 112, 2391-2393;
- (2000) Angew. Chem. , vol.112 , pp. 2391-2393

35
- 0034703713
- T. Bach, H. Bergmann, J. Am. Chem. Soc. 2000, 122, 11525-11526;
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 11525-11526
- Bach, T.¹ Bergmann, H.²

36
- 33644675697
- A. Furutani, K. Katayama, Y. Uesima, M. Ogura, Y. Tobe, H. Kurosawa, K. Tsutsumi, T. Morimoto, K. Kakiuchi, Chirality 2006, 18, 217-221;
- (2006) Chirality , vol.18 , pp. 217-221
- Furutani, A.¹ Katayama, K.² Uesima, Y.³ Ogura, M.⁴ Tobe, Y.⁵ Kurosawa, H.⁶ Tsutsumi, K.⁷ Morimoto, T.⁸ Kakiuchi, K.⁹

37
- 77950823167
- D. Albrecht, F. Vogt, T. Bach, Chem. Eur. J. 2010, 16, 4284-4296;
- (2010) Chem. Eur. J. , vol.16 , pp. 4284-4296
- Albrecht, D.¹ Vogt, F.² Bach, T.³

38
- 84885652033
- S. C. Coote, T. Bach, J. Am. Chem. Soc. 2013, 135, 14948-14951.
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 14948-14951
- Coote, S.C.¹ Bach, T.²

39
- 0000211039
- M. T. Crimmins, T. L. Reinhold, Org. React. 1993, 44, 297-588;
- (1993) Org. React. , vol.44 , pp. 297-588
- Crimmins, M.T.¹ Reinhold, T.L.²

40
- 0000346527
- in ed. E 21c (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart
- J. Mattay, R. Conrads, R. Hoffmann, in Methoden der Organischen Chemie (Houben-Weyl) 4th ed., Vol. E 21c (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann,), Thieme, Stuttgart 1995, pp. 3085-3132;
- (1995) Methoden der Organischen Chemie (Houben-Weyl) 4th , pp. 3085-3132
- Mattay, J.¹ Conrads, R.² Hoffmann, R.³

41
- 23044510752
- in (Eds.: A. G. Griesbeck, J. Mattay), Marcel Dekker, New York
- P. Margaretha, in Molecular and Supramolecular Photochemistry, Vol. 12 (Eds.:, A. G. Griesbeck, J. Mattay,), Marcel Dekker, New York, 2005, pp. 211-237;
- (2005) Molecular and Supramolecular Photochemistry , vol.12 , pp. 211-237
- Margaretha, P.¹

42
- 84885745589
- in (Eds.: A. Albini, M. Fagnoni), Wiley-VCH, Weinheim
- J. P. Hehn, C. Müller, T. Bach, in Handbook of Synthetic Photochemistry (Eds.:, A. Albini, M. Fagnoni,), Wiley-VCH, Weinheim, 2009, pp. 171-215.
- (2009) Handbook of Synthetic Photochemistry , pp. 171-215
- Hehn, J.P.¹ Müller, C.² Bach, T.³

43
- 70349895886
- C. Müller, A. Bauer, T. Bach, Angew. Chem. Int. Ed. 2009, 48, 6640-6642;
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 6640-6642
- Müller, C.¹ Bauer, A.² Bach, T.³

44
- 72449188976
- Angew. Chem. 2009, 121, 6767-6769;
- (2009) Angew. Chem. , vol.121 , pp. 6767-6769

45
- 78249281044
- H. Guo, E. Herdtweck, T. Bach, Angew. Chem. Int. Ed. 2010, 49, 7782-7785;
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 7782-7785
- Guo, H.¹ Herdtweck, E.² Bach, T.³

46
- 79956081661
- Angew. Chem. 2010, 122, 7948-7951;
- (2010) Angew. Chem. , vol.122 , pp. 7948-7951

47
- 80054730446
- C. Müller, A. Bauer, M. M. Maturi, M. C. Cuquerella, M. A. Miranda, T. Bach, J. Am. Chem. Soc. 2011, 133, 16689-16697;
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 16689-16697
- Müller, C.¹ Bauer, A.² Maturi, M.M.³ Cuquerella, M.C.⁴ Miranda, M.A.⁵ Bach, T.⁶

48
- 84887758589
- R. Brimioulle, T. Bach, Science 2013, 342, 840-843;
- (2013) Science , vol.342 , pp. 840-843
- Brimioulle, R.¹ Bach, T.²

49
- 84899024092
- R. Alonso, T. Bach, Angew. Chem. Int. Ed. 2014, 53, 4368-4371;
- (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 4368-4371
- Alonso, R.¹ Bach, T.²

50
- 84904475156
- Angew. Chem. 2014, 126, 4457-4460;
- (2014) Angew. Chem. , vol.126 , pp. 4457-4460

51
- 84899543979
- J. Du, K. L. Skubi, D. M. Schultz, T. P. Yoon, Science 2014, 344, 392-396;
- (2014) Science , vol.344 , pp. 392-396
- Du, J.¹ Skubi, K.L.² Schultz, D.M.³ Yoon, T.P.⁴

52
- 84901408665
- N. Vallavoju, S. Selvakumar, S. Jockusch, M. P. Sibi, J. Sivaguru, Angew. Chem. Int. Ed. 2014, 53, 5604-5608;
- (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 5604-5608
- Vallavoju, N.¹ Selvakumar, S.² Jockusch, S.³ Sibi, M.P.⁴ Sivaguru, J.⁵

53
- 84902677161
- Angew. Chem. 2014, 126, 5710-5714;
- (2014) Angew. Chem. , vol.126 , pp. 5710-5714

54
- 84904474115
- M. M. Maturi, T. Bach, Angew. Chem. Int. Ed. 2014, 53, 7661-7664;
- (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 7661-7664
- Maturi, M.M.¹ Bach, T.²

55
- 84911451573
- Angew. Chem. 2014, 126, 7793-7796.
- (2014) Angew. Chem. , vol.126 , pp. 7793-7796

56
- 84899551663
- Short overview
- Short overview:, R. Neier, Science 2014, 344, 368-369.
- (2014) Science , vol.344 , pp. 368-369
- Neier, R.¹

57
- 0000970604
- M. C. Pirrung, N. J. G. Webster, J. Org. Chem. 1987, 52, 3603-3613;
- (1987) J. Org. Chem. , vol.52 , pp. 3603-3613
- Pirrung, M.C.¹ Webster, N.J.G.²

58
- 0000912721
- J. Mattay, A. Banning, E. W. Bischof, A. Heidbreder, J. Runsink, Chem. Ber. 1992, 125, 2119-2127.
- (1992) Chem. Ber. , vol.125 , pp. 2119-2127
- Mattay, J.¹ Banning, A.² Bischof, E.W.³ Heidbreder, A.⁴ Runsink, J.⁵

59
- 84878215259
- Emission spectra:, M. M. Maturi, M. Wenninger, R. Alonso, A. Bauer, A. Pöthig, E. Riedle, T. Bach, Chem. Eur. J. 2013, 19, 7461-7472.
- (2013) Chem. Eur. J. , vol.19 , pp. 7461-7472
- Maturi, M.M.¹ Wenninger, M.² Alonso, R.³ Bauer, A.⁴ Pöthig, A.⁵ Riedle, E.⁶ Bach, T.⁷

60
- 84866998648
- 2 d:, D. A. Fort, T. J. Woltering, M. Nettekoven, H. Knust, T. Bach, Angew. Chem. Int. Ed. 2012, 51, 10169-10172;
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 10169-10172
- Fort, D.A.¹ Woltering, T.J.² Nettekoven, M.³ Knust, H.⁴ Bach, T.⁵

61
- 84875756448
- Angew. Chem. 2012, 124, 10316-10319;
- (2012) Angew. Chem. , vol.124 , pp. 10316-10319

62
- 37049123329
- 2 f
- 2 f:, Y. Tamura, H. Ishibashi, Y. Kita, M. Ikeda, J. Chem. Soc. Chem. Commun. 1973, 101-102.
- (1973) J. Chem. Soc. Chem. Commun. , pp. 101-102
- Tamura, Y.¹ Ishibashi, H.² Kita, Y.³ Ikeda, M.⁴

63
- 0038514123
- D. H. Ryu, E. J. Corey, J. Am. Chem. Soc. 2003, 125, 6388-6390;
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 6388-6390
- Ryu, D.H.¹ Corey, E.J.²

64
- 61949362917
- E. J. Corey, Angew. Chem. Int. Ed. 2009, 48, 2100-2117;
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 2100-2117
- Corey, E.J.¹

65
- 69449084660
- Angew. Chem. 2009, 121, 2134-2151;
- (2009) Angew. Chem. , vol.121 , pp. 2134-2151

66
- 84880616556
- R. C. Johnston, P. H.-Y. Cheong, Org. Biomol. Chem. 2013, 11, 5057-5064.
- (2013) Org. Biomol. Chem. , vol.11 , pp. 5057-5064
- Johnston, R.C.¹ Cheong, P.H.-Y.²

67
- 0025599951
- E. W. Bischof, J. Mattay, Tetrahedron Lett. 1990, 31, 7137-7140;
- (1990) Tetrahedron Lett. , vol.31 , pp. 7137-7140
- Bischof, E.W.¹ Mattay, J.²

68
- 0026033427
- J. Cossy, P. Aclinou, V. Bellosta, N. Furet, J. Baranne-Lafont, D. Sparfel, C. Souchaud, Tetrahedron Lett. 1991, 32, 1315-1316;
- (1991) Tetrahedron Lett. , vol.32 , pp. 1315-1316
- Cossy, J.¹ Aclinou, P.² Bellosta, V.³ Furet, N.⁴ Baranne-Lafont, J.⁵ Sparfel, D.⁶ Souchaud, C.⁷

69
- 33744820817
- W. D. Shipe, E. J. Sorensen, J. Am. Chem. Soc. 2006, 128, 7025-7035.
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 7025-7035
- Shipe, W.D.¹ Sorensen, E.J.²

70
- 0028768944
- For related ring-opening reactions of thermally generated cyclobutanes, see:, S. Yamago, A. Takeichi, E. Nakamura, J. Am. Chem. Soc. 1994, 116, 1123-1124.
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 1123-1124
- Yamago, S.¹ Takeichi, A.² Nakamura, E.³

71
- 0348042000
- M. Yu, B. L. Pagenkopf, Org. Lett. 2003, 5, 4639-4640;
- (2003) Org. Lett. , vol.5 , pp. 4639-4640
- Yu, M.¹ Pagenkopf, B.L.²

72
- 72449162551
- Review
- S. J. Gharpure, M. K. Shukla, U. Vijayasree, Org. Lett. 2009, 11, 5466-5469. Review:
- (2009) Org. Lett. , vol.11 , pp. 5466-5469
- Gharpure, S.J.¹ Shukla, M.K.² Vijayasree, U.³

73
- 0037884930
- H.-U. Reissig, R. Zimmer, Chem. Rev. 2003, 103, 1151-1196;
- (2003) Chem. Rev. , vol.103 , pp. 1151-1196
- Reissig, H.-U.¹ Zimmer, R.²

74
- 84892410356
- M. A. Cavitt, L. H. Phun, S. France, Chem. Soc. Rev. 2014, 43, 804-818.
- (2014) Chem. Soc. Rev. , vol.43 , pp. 804-818
- Cavitt, M.A.¹ Phun, L.H.² France, S.³

75
- 3343000016
- H. O. House, G. S. Nomura, D. VanDerveer, J. E. Wissinger, J. Org. Chem. 1986, 51, 2408-2416;
- (1986) J. Org. Chem. , vol.51 , pp. 2408-2416
- House, H.O.¹ Nomura, G.S.² VanDerveer, D.³ Wissinger, J.E.⁴

76
- 0000401819
- C. Mehta, N. Krishnamurthy, S. R. Karra, J. Am. Chem. Soc. 1991, 113, 5765-5775.
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 5765-5775
- Mehta, C.¹ Krishnamurthy, N.² Karra, S.R.³

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