SCOPUS 정보 검색 플랫폼

Chemical Communications

Volumn 52, Issue 14, 2016, Pages 2909-2912

Synergistic gold and enamine catalysis: Intermolecular α-alkylation of aldehydes with allenamides

(4) Fernández Casado, Jaime a Nelson, Ronald a Mascareñas, José L a López, Fernando a,b

a s n (Spain)

b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALLENAMIDE DERIVATIVE; AMIDE; AMINE; ENAMINE; GOLD; UNCLASSIFIED DRUG;

ALDOL REACTION; ALKYLATION; ALLYLATION; ANNULATION REACTION; ARTICLE; CATALYSIS; CATALYST; CHIRALITY; CONTROLLED STUDY; ELECTRON TRANSPORT; ELECTROPHILICITY; ENANTIOSELECTIVITY; ISOMERIZATION; LOW TEMPERATURE; POLYMERIZATION; REACTION TIME;

EID: 84957990015 PISSN: 13597345 EISSN: 1364548X Source Type: Journal
DOI: 10.1039/c5cc09533f Document Type: Article

Times cited : (33)

References (59)

1
- 84884908098
- ed., John Wiley & Sons
- Stereoselective Organocatalysis, ed., R. Rios, John Wiley & Sons, 2013
- (2013) Stereoselective Organocatalysis
- Rios, R.¹

2
- 84868374592
- ed., Georg Thieme Verlag KG, Stuttgart
- Science of Synthesis: Asymmetric Organocatalysis, ed., B. List, Georg Thieme Verlag KG, Stuttgart, 2012, vol. 1
- (2012) Science of Synthesis: Asymmetric Organocatalysis , vol.1
- List, B.¹

3
- 84884908098
- in, ed. R. Rios, John Wiley & Sons, For notable exceptions using alkyl halides, see
- M. RemeŠ and J. Veselý, in Stereoselective Organocatalysis, ed., R. Rios, John Wiley & Sons, 2013, pp. 267-312
- (2013) Stereoselective Organocatalysis , pp. 267-312
- Remeš, M.¹ Veselý, J.²

4
- 0345825852
- N. Vignola B. List J. Am. Chem. Soc. 2004 126 450
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 450
- Vignola, N.¹ List, B.²

5
- 54749100733
- D. Enders C. Wang J. W. Bats Angew. Chem., Int. Ed. 2008 47 7539
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 7539
- Enders, D.¹ Wang, C.² Bats, J.W.³

6
- 53849138773
- I. Ibrahem G.-L. Zhao R. Rios J. Vesely H. Sundén P. Dziedzic A. Córdova Chem.-Eur. J. 2008 14 7867
- (2008) Chem.-Eur. J. , vol.14 , pp. 7867
- Ibrahem, I.¹ Zhao, G.-L.² Rios, R.³ Vesely, J.⁴ Sundén, H.⁵ Dziedzic, P.⁶ Córdova, A.⁷

7
- 84890926781
- N1 processes), see
- B. List I. Čorić O. O. Grygorenko P. S. J. Kaib I. Komarov A. Lee M. Leutzsch S. C. Pan A. V. Tymtsunik M. van Gemmeren Angew. Chem., Int. Ed. 2014 53 282
- (2014) Angew. Chem., Int. Ed. , vol.53 , pp. 282
- List, B.¹ Čorić, I.² Grygorenko, O.O.³ Kaib, P.S.J.⁴ Komarov, I.⁵ Lee, A.⁶ Leutzsch, M.⁷ Pan, S.C.⁸ Tymtsunik, A.V.⁹ Van Gemmeren, M.¹⁰

8
- 34247565955
- T. D. Beeson A. Mastracchio J.-B. Hong K. Ashton D. W. C. MacMillan Science 2007 316 582
- (2007) Science , vol.316 , pp. 582
- Beeson, T.D.¹ Mastracchio, A.² Hong, J.-B.³ Ashton, K.⁴ MacMillan, D.W.C.⁵

9
- 77957304088
- H. W. Shih M. N. Vander Wal R. L. Grange D. W. C. MacMillan J. Am. Chem. Soc. 2010 132 13600
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 13600
- Shih, H.W.¹ Vander Wal, M.N.² Grange, R.L.³ MacMillan, D.W.C.⁴

10
- 84938424029
- E. R. Welin A. A. Warkentin J. C. Conrad D. W. C. MacMillan Angew. Chem., Int. Ed. 2015 54 9668
- (2015) Angew. Chem., Int. Ed. , vol.54 , pp. 9668
- Welin, E.R.¹ Warkentin, A.A.² Conrad, J.C.³ MacMillan, D.W.C.⁴

11
- 55249108726
- R. R. Shaikh A. Mazzanti M. Petrini G. Bartoli P. Melchiorre Angew. Chem., Int. Ed. 2008 47 8707
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 8707
- Shaikh, R.R.¹ Mazzanti, A.² Petrini, M.³ Bartoli, G.⁴ Melchiorre, P.⁵

12
- 60149108649
- P. G. Cozzi F. Benfatti L. Zoli Angew. Chem., Int. Ed. 2009 48 1313
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 1313
- Cozzi, P.G.¹ Benfatti, F.² Zoli, L.³

13
- 77955816969
- A. R. Brown W.-H. Kuo E. N. Jacobsen J. Am. Chem. Soc. 2010 132 9286
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 9286
- Brown, A.R.¹ Kuo, W.-H.² Jacobsen, E.N.³

14
- 84935009621
- R. Dorel A. M. Echavarren Chem. Rev. 2015 115 9028
- (2015) Chem. Rev. , vol.115 , pp. 9028
- Dorel, R.¹ Echavarren, A.M.²

15
- 84898012143
- W. Yang A. S. K. Hashmi Chem. Soc. Rev. 2014 43 2941
- (2014) Chem. Soc. Rev. , vol.43 , pp. 2941
- Yang, W.¹ Hashmi, A.S.K.²

16
- 84924263403
- M. Jia M. Bandini ACS Catal. 2015 5 1638
- (2015) ACS Catal. , vol.5 , pp. 1638
- Jia, M.¹ Bandini, M.²

17
- 70350496890
- For a definition of synergistic catalysis as a process "wherein two catalysts and two catalytic cycles work in concert to create a new single bond", see
- A. Fürstner Chem. Soc. Rev. 2009 38 3208
- (2009) Chem. Soc. Rev. , vol.38 , pp. 3208
- Fürstner, A.¹

18
- 84857350578
- See also
- A. E. Allen D. W. Macmillan Chem. Sci. 2012 3 633
- (2012) Chem. Sci. , vol.3 , pp. 633
- Allen, A.E.¹ MacMillan, D.W.²

19
- 84897109052
- A. Gualandi L. Mengozzi C. M. Wilson P. G. Cozzi Chem.-Asian J. 2014 9 984
- (2014) Chem.-Asian J. , vol.9 , pp. 984
- Gualandi, A.¹ Mengozzi, L.² Wilson, C.M.³ Cozzi, P.G.⁴

20
- 84897146621
- Y. Deng S. Kumar H. Wang Chem. Commun. 2014 50 4272
- (2014) Chem. Commun. , vol.50 , pp. 4272
- Deng, Y.¹ Kumar, S.² Wang, H.³

21
- 84872744548
- Z. Du Z. Shao Chem. Soc. Rev. 2013 42 1337
- (2013) Chem. Soc. Rev. , vol.42 , pp. 1337
- Du, Z.¹ Shao, Z.²

22
- 76249126612
- For selected, more recent examples, see
- A. S. K. Hashmi C. Hubbert Angew. Chem., Int. Ed. 2010 49 1010
- (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 1010
- Hashmi, A.S.K.¹ Hubbert, C.²

23
- 84937692381
- H. H. Peng N. G. Akhmedov Y. F. Liang N. Jiao X. Shi J. Am. Chem. Soc. 2015 137 8912
- (2015) J. Am. Chem. Soc. , vol.137 , pp. 8912
- Peng, H.H.¹ Akhmedov, N.G.² Liang, Y.F.³ Jiao, N.⁴ Shi, X.⁵

24
- 84896870944
- S. Krautwald M. A. Schafroth D. Sarlah E. M. Carreira J. Am. Chem. Soc. 2014 136 3020
- (2014) J. Am. Chem. Soc. , vol.136 , pp. 3020
- Krautwald, S.¹ Schafroth, M.A.² Sarlah, D.³ Carreira, E.M.⁴

25
- 84899024176
- R. Shibuya L. Lin Y. Nakahara K. Mashima T. Ohshima Angew. Chem., Int. Ed. 2014 53 4377
- (2014) Angew. Chem., Int. Ed. , vol.53 , pp. 4377
- Shibuya, R.¹ Lin, L.² Nakahara, Y.³ Mashima, K.⁴ Ohshima, T.⁵

26
- 84882271547
- J. M. Stevens D. W. C. MacMillan J. Am. Chem. Soc. 2013 135 11756
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 11756
- Stevens, J.M.¹ MacMillan, D.W.C.²

27
- 84878349078
- For a review highlighting the challenges of synergistic dual enamine/gold catalysis see
- S. Krautwald D. Sarlah M. A. Schafroth E. M. Carreira Science 2013 340 1065
- (2013) Science , vol.340 , pp. 1065
- Krautwald, S.¹ Sarlah, D.² Schafroth, M.A.³ Carreira, E.M.⁴

28
- 84862768307
- see also ref. 6b and c
- C. C. Loh D. Enders Chem.-Eur. J. 2012 18 10212
- (2012) Chem.-Eur. J. , vol.18 , pp. 10212
- Loh, C.C.¹ Enders, D.²

29
- 84864487708
- M. Chiarucci M. di Lillo A. Romaniello P. G. Cozzi G. Cera M. Bandini Chem. Sci. 2012 3 2859
- (2012) Chem. Sci. , vol.3 , pp. 2859
- Chiarucci, M.¹ Di Lillo, M.² Romaniello, A.³ Cozzi, P.G.⁴ Cera, G.⁵ Bandini, M.⁶

30
- 45549094465
- J. T. Binder B. Crone T. T. Haug H. Menz S. F. Kirsch Org. Lett. 2008 10 1025
- (2008) Org. Lett. , vol.10 , pp. 1025
- Binder, J.T.¹ Crone, B.² Haug, T.T.³ Menz, H.⁴ Kirsch, S.F.⁵

31
- 75749120984
- K. L. Jensen P. T. Franke C. Arroniz S. Kobbelgaard K. A. Jorgensen Chem.-Eur. J. 2010 16 1750
- (2010) Chem.-Eur. J. , vol.16 , pp. 1750
- Jensen, K.L.¹ Franke, P.T.² Arroniz, C.³ Kobbelgaard, S.⁴ Jorgensen, K.A.⁵

32
- 84890743941
- See also
- Z. Wang X. Li Y. Huang Angew. Chem., Int. Ed. 2013 52 14219
- (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 14219
- Wang, Z.¹ Li, X.² Huang, Y.³

33
- 84906879111
- For selected examples, see
- Z. Wang L. Li Y. Huang J. Am. Chem. Soc. 2014 136 12233
- (2014) J. Am. Chem. Soc. , vol.136 , pp. 12233
- Wang, Z.¹ Li, L.² Huang, Y.³

34
- 84862579220
- H. Faustino P. Bernal L. Castedo F. López J. L. Mascareñas Adv. Synth. Catal. 2012 354 1658
- (2012) Adv. Synth. Catal. , vol.354 , pp. 1658
- Faustino, H.¹ Bernal, P.² Castedo, L.³ López, F.⁴ Mascareñas, J.L.⁵

35
- 84868571319
- S. Suárez-Pantiga C. Hernández-Díaz E. Rubio J. M. González Angew. Chem., Int. Ed. 2012 51 11552
- (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 11552
- Suárez-Pantiga, S.¹ Hernández-Díaz, C.² Rubio, E.³ González, J.M.⁴

36
- 84878927202
- H. Faustino I. Alonso J. L. Mascareñas F. López Angew. Chem., Int. Ed. 2013 52 6526
- (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 6526
- Faustino, H.¹ Alonso, I.² Mascareñas, J.L.³ López, F.⁴

37
- 84877252396
- G. H. Li W. Zhou X. X. Li Q. W. Bi Z. Wang Z. G. Zhao W. X. Hu Z. Chen Chem. Commun. 2013 49 4770
- (2013) Chem. Commun. , vol.49 , pp. 4770
- Li, G.H.¹ Zhou, W.² Li, X.X.³ Bi, Q.W.⁴ Wang, Z.⁵ Zhao, Z.G.⁶ Hu, W.X.⁷ Chen, Z.⁸

38
- 84941661952
- Y. D. Wang P. C. Zhang Y. Liu F. Xia J. Zhang Chem. Sci. 2015 6 5564
- (2015) Chem. Sci. , vol.6 , pp. 5564
- Wang, Y.D.¹ Zhang, P.C.² Liu, Y.³ Xia, F.⁴ Zhang, J.⁵

39
- 84947207549
- L. Rocchigiani M. Jia M. Bandini A. Macchioni ACS Catal. 2015 5 3911
- (2015) ACS Catal. , vol.5 , pp. 3911
- Rocchigiani, L.¹ Jia, M.² Bandini, M.³ MacChioni, A.⁴

40
- 84928168472
- H. Faustino I. Varela J. L. Mascareñas F. López Chem. Sci. 2015 6 2903
- (2015) Chem. Sci. , vol.6 , pp. 2903
- Faustino, H.¹ Varela, I.² Mascareñas, J.L.³ López, F.⁴

41
- 77749298161
- M. C. Kimber Org. Lett. 2010 12 1128
- (2010) Org. Lett. , vol.12 , pp. 1128
- Kimber, M.C.¹

42
- 68149092549
- A. G. Lohse R. P. Hsung Org. Lett. 2009 11 3430
- (2009) Org. Lett. , vol.11 , pp. 3430
- Lohse, A.G.¹ Hsung, R.P.²

43
- 84983097418
- Y. Wang P. Zhang D. Qian J. Zhang Angew. Chem., Int. Ed. 2015 54 14849
- (2015) Angew. Chem., Int. Ed. , vol.54 , pp. 14849
- Wang, Y.¹ Zhang, P.² Qian, D.³ Zhang, J.⁴

44
- 84916210114
- P. Bernal-Albert H. Faustino A. Gimeno G. Asensio J. L. Mascareñas F. López Org. Lett. 2014 16 6196
- (2014) Org. Lett. , vol.16 , pp. 6196
- Bernal-Albert, P.¹ Faustino, H.² Gimeno, A.³ Asensio, G.⁴ Mascareñas, J.L.⁵ López, F.⁶

45
- 79955576875
- H. Faustino F. López L. Castedo J. L. Mascareñas Chem. Sci. 2011 2 633
- (2011) Chem. Sci. , vol.2 , pp. 633
- Faustino, H.¹ López, F.² Castedo, L.³ Mascareñas, J.L.⁴

46
- 84880085348
- T. Lu Z. Lu Z. X. Ma Y. Zhang R. P. Hsung Chem. Rev. 2013 113 4862
- (2013) Chem. Rev. , vol.113 , pp. 4862
- Lu, T.¹ Lu, Z.² Ma, Z.X.³ Zhang, Y.⁴ Hsung, R.P.⁵

47
- 0142213273
- L.-L. Wei H. Xiong R. P. Hsung Acc. Chem. Res. 2003 36 773
- (2003) Acc. Chem. Res. , vol.36 , pp. 773
- Wei, L.-L.¹ Xiong, H.² Hsung, R.P.³

48
- 84886640879
- It has been widely described that the interaction between Au(i) complexes and amines affects their catalytic properties, see
- S. Montserrat H. Faustino A. Lledós J. L. Mascareñas F. López G. Ujaque Chem.-Eur. J. 2013 19 15248
- (2013) Chem.-Eur. J. , vol.19 , pp. 15248
- Montserrat, S.¹ Faustino, H.² Lledós, A.³ Mascareñas, J.L.⁴ López, F.⁵ Ujaque, G.⁶

49
- 84881043675
- P. C. Young S. L. J. Green G. M. Rosair A. L. Lee Dalton Trans. 2013 42 9645
- (2013) Dalton Trans. , vol.42 , pp. 9645
- Young, P.C.¹ Green, S.L.J.² Rosair, G.M.³ Lee, A.L.⁴

50
- 84903794801
- Int. Ed. For gold(i)-enamine complexes, see
- A. Grirrane E. Álvarez H. García A. Corma Angew. Chem., Int. Ed. 2014 53 7253
- (2014) Angew. Chem. , vol.53 , pp. 7253
- Grirrane, A.¹ Álvarez, E.² García, H.³ Corma, A.⁴

51
- 84906568957
- M. Sriram Y. Y. Zhu A. M. Camp C. S. Day A. C. Jones Organometallics 2014 33 4157
- (2014) Organometallics , vol.33 , pp. 4157
- Sriram, M.¹ Zhu, Y.Y.² Camp, A.M.³ Day, C.S.⁴ Jones, A.C.⁵

52
- 84904612536
- A. Zhdanko M. E. Maier Angew. Chem., Int. Ed. 2014 53 7760
- (2014) Angew. Chem., Int. Ed. , vol.53 , pp. 7760
- Zhdanko, A.¹ Maier, M.E.²

53
- 84862908802
- see also ref. 12a
- X. X. Li L. L. Zhu W. Zhou Z. Chen Org. Lett. 2012 14 436
- (2012) Org. Lett. , vol.14 , pp. 436
- Li, X.X.¹ Zhu, L.L.² Zhou, W.³ Chen, Z.⁴

54
- 0032491089
- 2 or the benzotriazole-based catalysts improves the stability of the Au(i) species in the presence of water and acids, see
- K. Takagi I. Tomita T. Endo Macromolecules 1998 31 6741
- (1998) Macromolecules , vol.31 , pp. 6741
- Takagi, K.¹ Tomita, I.² Endo, T.³

55
- 84924263403
- M. Jia M. Bandini ACS Catal. 2015 5 1638
- (2015) ACS Catal. , vol.5 , pp. 1638
- Jia, M.¹ Bandini, M.²

56
- 80051534195
- 2 or HOTf instead of the gold catalyst did not lead to the formation of the product 3aa 18 This E/Z isomerization has only been observed when 2-arylacetaldehydes are used as substrates
- D. Wang Y. Zhang R. Cai X. Shi Beilstein J. Org. Chem. 2011 7 1014
- (2011) Beilstein J. Org. Chem. , vol.7 , pp. 1014
- Wang, D.¹ Zhang, Y.² Cai, R.³ Shi, X.⁴

57
- 84858633852
- 6, see
- K. L. Jensen G. Dickmeiss H. Jiang L. Albrecht K. A. Jorgensen Acc. Chem. Res. 2012 45 248
- (2012) Acc. Chem. Res. , vol.45 , pp. 248
- Jensen, K.L.¹ Dickmeiss, G.² Jiang, H.³ Albrecht, L.⁴ Jorgensen, K.A.⁵

58
- 0037571492
- See also
- W. Clegg Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 1976 32 2712
- (1976) Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. , vol.32 , pp. 2712
- Clegg, W.¹

59
- 84947866890
- 2 became more evident by ESI, further confirming the equilibrium 18
- R. Cai M. Lu E. Y. Aguilera Y. M. Xi N. G. Akhmedov J. L. Petersen H. Chen X. Shi Angew. Chem., Int. Ed. 2015 54 8772
- (2015) Angew. Chem., Int. Ed. , vol.54 , pp. 8772
- Cai, R.¹ Lu, M.² Aguilera, E.Y.³ Xi, Y.M.⁴ Akhmedov, N.G.⁵ Petersen, J.L.⁶ Chen, H.⁷ Shi, X.⁸

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.