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Chemistry - A European Journal

Volumn 17, Issue 33, 2011, Pages 9037-9041

Direct enantioselective amination of α-ketoesters catalyzed by an axially chiral guanidine base

(5) Terada, Masahiro a Amagai, Kei a Ando, Kenichi a Kwon, Eunsang a Ube, Hitoshi b

a TOHOKU UNIVERSITY (Japan)

b UNIVERSITY OF TOKYO (Japan)

Author keywords

amino alcohols; asymmetric catalysis; enantioselectivity; guanidine; organocatalysis

Indexed keywords

ALIPHATIC SUBSTITUENTS; AMINO ALCOHOLS; ASYMMETRIC CATALYSIS; AZODICARBOXYLATES; BASE CATALYST; DIASTEREO- AND ENANTIOSELECTIVITY; ENANTIOSELECTIVE; GUANIDINE; HYDROXY ESTERS; KETO ESTER; NUCLEOPHILIC ADDITIONS; ORGANOCATALYSIS;

ADDITION REACTIONS; ALCOHOLS; AMINATION; CATALYSIS; ENANTIOSELECTIVITY; KETONES; REACTION KINETICS;

AMINES;

AMINOALCOHOL; ESTER; GUANIDINE; KETONE;

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

AMINATION; AMINO ALCOHOLS; CATALYSIS; ESTERS; GUANIDINE; KETONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 79961184071 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.201101076 Document Type: Article

Times cited : (35)

References (67)

1
- 51049122384
- For a recent review, see
- For a recent review, see:, M. Shibasaki, M. Kanai, Chem. Rev. 2008, 108, 2853-2873.
- (2008) Chem. Rev. , vol.108 , pp. 2853-2873
- Shibasaki, M.¹ Kanai, M.²

2
- 0030952586
- For selected examples, see: (a) D. A. Evans, M. C. Kozlowski, C. S. Burgey, D. W. C. MacMillan, J. Am. Chem. Soc. 1997, 119, 7893-7894
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 7893-7894
- Evans, D.A.¹ Kozlowski, M.C.² Burgey, C.S.³ MacMillan, D.W.C.⁴

3
- 0030781007
- D. A. Evans, D. W. C. MacMillan, K. R. Campos, J. Am. Chem. Soc. 1997, 119, 10859-10860
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 10859-10860
- Evans, D.A.¹ MacMillan, D.W.C.² Campos, K.R.³

4
- 0002816322
- M. Johannsen, S. Yao, K. A. Jørgensen, Chem. Commun. 1997, 2169-2170
- (1997) Chem. Commun. , pp. 2169-2170
- Johannsen, M.¹ Yao, S.² Jørgensen, K.A.³

5
- 0032475445
- S. Yao, M. Johannsen, H. Audrain, R. G. Hazell, K. A. Jørgensen, J. Am. Chem. Soc. 1998, 120, 8599-8605
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 8599-8605
- Yao, S.¹ Johannsen, M.² Audrain, H.³ Hazell, R.G.⁴ Jørgensen, K.A.⁵

6
- 0034706033
- D. A. Evans, S. W. Tregay, C. S. Burgey, N. A. Paras, T. Vojkovsky, J. Am. Chem. Soc. 2000, 122, 7936-7943
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 7936-7943
- Evans, D.A.¹ Tregay, S.W.² Burgey, C.S.³ Paras, N.A.⁴ Vojkovsky, T.⁵

7
- 0034703753
- H. Audrain, K. A. Jørgensen, J. Am. Chem. Soc. 2000, 122, 11543-11544
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 11543-11544
- Audrain, H.¹ Jørgensen, K.A.²

8
- 2242447409
- P. I. Dalko, L. Moisan, J. Cossy, Angew. Chem. 2002, 114, 647-650
- (2002) Angew. Chem. , vol.114 , pp. 647-650
- Dalko, P.I.¹ Moisan, L.² Cossy, J.³

9
- 0037083878
- Angew. Chem. Int. Ed. 2002, 41, 625-628
- (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 625-628

10
- 0037132621
- H. Suga, K. Inoue, S. Inoue, A. Kakehi, J. Am. Chem. Soc. 2002, 124, 14836-14837
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 14836-14837
- Suga, H.¹ Inoue, K.² Inoue, S.³ Kakehi, A.⁴

11
- 0142106406
- D. Yang, M. Yang, N.-Y. Zhu, Org. Lett. 2003, 5, 3749-3752
- (2003) Org. Lett. , vol.5 , pp. 3749-3752
- Yang, D.¹ Yang, M.² Zhu, N.-Y.³

12
- 33746825711
- N. A. Caplan, F. E. Hancock, P. Bulman, C. Philip, G. J. Hutchings, Angew. Chem. 2004, 116, 1717-1720
- (2004) Angew. Chem. , vol.116 , pp. 1717-1720
- Caplan, N.A.¹ Hancock, F.E.² Bulman, P.³ Philip, C.⁴ Hutchings, G.J.⁵

13
- 4544385176
- Angew. Chem. Int. Ed. 2004, 43, 1685-1688
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 1685-1688

14
- 22544465610
- M. Langner, C. Bolm, Angew. Chem. 2004, 116, 6110-6113
- (2004) Angew. Chem. , vol.116 , pp. 6110-6113
- Langner, M.¹ Bolm, C.²

15
- 9244221087
- Angew. Chem. Int. Ed. 2004, 43, 5984-5987
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 5984-5987

16
- 8744245317
- J. Cong-Dung Le, B. L. Pagenkopf, Org. Lett. 2004, 6, 4097-4099
- (2004) Org. Lett. , vol.6 , pp. 4097-4099
- Cong-Dung Le, J.¹ Pagenkopf, B.L.²

17
- 27644550057
- L. C. Wieland, H. Deng, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2005, 127, 15453-15456
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 15453-15456
- Wieland, L.C.¹ Deng, H.² Snapper, M.L.³ Hoveyda, A.H.⁴

18
- 33646439546
- P. Rémy, M. Langner, C. Bolm, Org. Lett. 2006, 8, 1209-1211
- (2006) Org. Lett. , vol.8 , pp. 1209-1211
- Rémy, P.¹ Langner, M.² Bolm, C.³

19
- 35848952527
- K. Mikami, Y. Kawakami, K. Akiyama, K. Aikawa, J. Am. Chem. Soc. 2007, 129, 12950-12951
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 12950-12951
- Mikami, K.¹ Kawakami, Y.² Akiyama, K.³ Aikawa, K.⁴

20
- 68949098579
- A. Yanagisawa, Y. Terajima, K. Sugita, K. Yoshida, Adv. Synth. Catal. 2009, 351, 1757-1762
- (2009) Adv. Synth. Catal. , vol.351 , pp. 1757-1762
- Yanagisawa, A.¹ Terajima, Y.² Sugita, K.³ Yoshida, K.⁴

21
- 77950843946
- M. Frings, I. Atodiresei, Y. Wang, J. Runsink, G. Raabe, C. Bolm, Chem. Eur. J. 2010, 16, 4577-4587
- (2010) Chem. Eur. J. , vol.16 , pp. 4577-4587
- Frings, M.¹ Atodiresei, I.² Wang, Y.³ Runsink, J.⁴ Raabe, G.⁵ Bolm, C.⁶

22
- 77954767740
- M. Frings, D. Goedert, C. Bolm, Chem. Commun. 2010, 46, 5497-5499.
- (2010) Chem. Commun. , vol.46 , pp. 5497-5499
- Frings, M.¹ Goedert, D.² Bolm, C.³

23
- 31444439419
- For recent examples, see: (a) H. Li, B. Wang, L. Deng, J. Am. Chem. Soc. 2006, 128, 732-733
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 732-733
- Li, H.¹ Wang, B.² Deng, L.³

24
- 33645915448
- Z. Tang, L.-F. Cun, X. Cui, A.-Q. Mi, Y.-Z. Jiang, L.-Z. Gong, Org. Lett. 2006, 8, 1263-1266
- (2006) Org. Lett. , vol.8 , pp. 1263-1266
- Tang, Z.¹ Cun, L.-F.² Cui, X.³ Mi, A.-Q.⁴ Jiang, Y.-Z.⁵ Gong, L.-Z.⁶

25
- 33748923813
- H. Li, Y.-Q. Wang, L. Deng, Org. Lett. 2006, 8, 4063-4065
- (2006) Org. Lett. , vol.8 , pp. 4063-4065
- Li, H.¹ Wang, Y.-Q.² Deng, L.³

26
- 56749102623
- C. Zheng, Y. Wu, X. Wang, G. Zhao, Adv. Synth. Catal. 2008, 350, 2690-2694
- (2008) Adv. Synth. Catal. , vol.350 , pp. 2690-2694
- Zheng, C.¹ Wu, Y.² Wang, X.³ Zhao, G.⁴

27
- 67549099242
- M. Raj, G. S. Parashari, V. K. Singh, Adv. Synth. Catal. 2009, 351, 1284-1288
- (2009) Adv. Synth. Catal. , vol.351 , pp. 1284-1288
- Raj, M.¹ Parashari, G.S.² Singh, V.K.³

28
- 75649088899
- V. B. Gondi, K. Hagihara, V. H. Rawal, Chem. Commun. 2010, 46, 904-906
- (2010) Chem. Commun. , vol.46 , pp. 904-906
- Gondi, V.B.¹ Hagihara, K.² Rawal, V.H.³

29
- 77950207491
- X. Jiang, G. Zhang, D. Fu, Y. Cao, F. Shen, R. Wang, Org. Lett. 2010, 12, 1544-1547
- (2010) Org. Lett. , vol.12 , pp. 1544-1547
- Jiang, X.¹ Zhang, G.² Fu, D.³ Cao, Y.⁴ Shen, F.⁵ Wang, R.⁶

30
- 77956021172
- M. Vecchione, L. Li, D. Seidel, Chem. Commun. 2010, 46, 4604-4606.
- (2010) Chem. Commun. , vol.46 , pp. 4604-4606
- Vecchione, M.¹ Li, L.² Seidel, D.³

31
- 0000119848
- For chiral metal catalysts. α-Ketoesters, see: (a) K. Juhl, N. Gathergood, K. A. Jørgensen, Angew. Chem. 2001, 113, 3083-3085
- (2001) Angew. Chem. , vol.113 , pp. 3083-3085
- Juhl, K.¹ Gathergood, N.² Jørgensen, K.A.³

32
- 0035902842
- Angew. Chem. Int. Ed. 2001, 40, 2995-2997
- (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 2995-2997

33
- 0037139602
- K. Juhl, K. A. Jørgensen, J. Am. Chem. Soc. 2002, 124, 2420-2421
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 2420-2421
- Juhl, K.¹ Jørgensen, K.A.²

34
- 2342646154
- N. Gathergood, K. Juhl, T. B. Poulsen, K. Thordrup, K. A. Jørgensen, Org. Biomol. Chem. 2004, 2, 1077-1085
- (2004) Org. Biomol. Chem. , vol.2 , pp. 1077-1085
- Gathergood, N.¹ Juhl, K.² Poulsen, T.B.³ Thordrup, K.⁴ Jørgensen, K.A.⁵

35
- 77950262715
- Ketoanilides, see
- A. Nakamura, S. Lectard, D. Hashizume, Y. Hamashima, M. Sodeoka, J. Am. Chem. Soc. 2010, 132, 4036-4037. α-Ketoanilides, see
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 4036-4037
- Nakamura, A.¹ Lectard, S.² Hashizume, D.³ Hamashima, Y.⁴ Sodeoka, M.⁵

36
- 65349192729
- G. Lu, H. Morimoto, S. Matsunaga, M. Shibasaki, Angew. Chem. 2008, 120, 6953-6956
- (2008) Angew. Chem. , vol.120 , pp. 6953-6956
- Lu, G.¹ Morimoto, H.² Matsunaga, S.³ Shibasaki, M.⁴

37
- 52449119278
- Angew. Chem. Int. Ed. 2008, 47, 6847-6850.
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 6847-6850

38
- 5144234219
- For organocatalysts, see: (a) H. Torii, M. Nakadai, K. Ishihara, S. Saito, H. Yamamoto, Angew. Chem. 2004, 116, 2017-2020
- (2004) Angew. Chem. , vol.116 , pp. 2017-2020
- Torii, H.¹ Nakadai, M.² Ishihara, K.³ Saito, S.⁴ Yamamoto, H.⁵

39
- 2942641357
- Angew. Chem. Int. Ed. 2004, 43, 1983-1986
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 1983-1986

40
- 36148951302
- J.-M. Vincent, C. Morgottin, M. Berlande, D. Cavagnat, T. Buffeteau, Y. Landais, Chem. Commun. 2007, 4782-4784.
- (2007) Chem. Commun. , pp. 4782-4784
- Vincent, J.-M.¹ Morgottin, C.² Berlande, M.³ Cavagnat, D.⁴ Buffeteau, T.⁵ Landais, Y.⁶

41
- 0034700224
- For chiral metal catalyst, see: (a) K. Juhl, N. Gathergood, K. A. Jørgensen, Chem. Commun. 2000, 2211-2212. For organocatalyst, see
- (2000) Chem. Commun. , pp. 2211-2212
- Juhl, K.¹ Gathergood, N.² Jørgensen, K.A.³

42
- 27144545042
- P. Dambruoso, A. Massi, A. Dondoni, Org. Lett. 2005, 7, 4657-4660.
- (2005) Org. Lett. , vol.7 , pp. 4657-4660
- Dambruoso, P.¹ Massi, A.² Dondoni, A.³

43
- 47749122232
- Wiley-VCH, Weinheim
- For recent reviews, see: (a) A. Berkessel, H. Gröger, Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis, Wiley-VCH, Weinheim, 2005
- (2005) Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis
- Berkessel, A.¹ Gröger, H.²

44
- 55049138759
- Wiley-VCH, Weinheim
- Enantioselective Organocatalysis: Reactions and Experimental Procedures (Ed.:, P. I. Dalko,), Wiley-VCH, Weinheim, 2007
- (2007) Enantioselective Organocatalysis: Reactions and Experimental Procedures
- Dalko, P.I.¹

45
- 84891505647
- Wiley-VCH, Weinheim
- Hydrogen Bonding in Organic Synthesis (Ed.:, P. M. Pihko,), Wiley-VCH, Weinheim, 2009
- (2009) Hydrogen Bonding in Organic Synthesis
- Pihko, P.M.¹

46
- 79961196572
- Springer, Berlin
- Topics in Current Chemistry, Vol. 291: Asymmetric Organocatalysis (Ed.:, B. List,), Springer, Berlin, 2009
- (2009) Topics in Current Chemistry: Asymmetric Organocatalysis , vol.291
- List, B.¹

47
- 78649322702
- Royal Society of Chemistry Publishing, Cambridge
- H. Pellissier, Recent Developments in Asymmetric Organocatalysis, Royal Society of Chemistry Publishing, Cambridge, 2010.
- (2010) Recent Developments in Asymmetric Organocatalysis
- Pellissier, H.¹

48
- 33746848929
- For a review of electrophilic amination of carbonyl compounds, see
- For a review of electrophilic amination of carbonyl compounds, see:, G. Guillena, D. J. Ramõn, Tetrahedron: Asymmetry 2006, 17, 1465-1492.
- (2006) Tetrahedron: Asymmetry , vol.17 , pp. 1465-1492
- Guillena, G.¹ Ramõn, D.J.²

49
- 32244444791
- M. Terada, H. Ube, Y. Yaguchi, J. Am. Chem. Soc. 2006, 128, 1454-1455
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 1454-1455
- Terada, M.¹ Ube, H.² Yaguchi, Y.³

50
- 36448993352
- M. Terada, T. Ikehara, H. Ube, J. Am. Chem. Soc. 2007, 129, 14112-14113
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 14112-14113
- Terada, M.¹ Ikehara, T.² Ube, H.³

51
- 61349131461
- M. Terada, M. Nakano, Heterocycles 2008, 76, 1049-1055
- (2008) Heterocycles , vol.76 , pp. 1049-1055
- Terada, M.¹ Nakano, M.²

52
- 79551488904
- H. Ube, N. Shimada, M. Terada, Angew. Chem. 2010, 122, 1902-1905
- (2010) Angew. Chem. , vol.122 , pp. 1902-1905
- Ube, H.¹ Shimada, N.² Terada, M.³

53
- 77749309286
- Angew. Chem. Int. Ed. 2010, 49, 1858-1861
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 1858-1861

54
- 79551486283
- M. Terada, H. Nii, Chem. Eur. J. 2011, 17, 1760-1763
- (2011) Chem. Eur. J. , vol.17 , pp. 1760-1763
- Terada, M.¹ Nii, H.²

55
- 79955445667
- Also see
- M. Terada, K. Ando, Org. Lett. 2011, 13, 2026-2029. Also see
- (2011) Org. Lett. , vol.13 , pp. 2026-2029
- Terada, M.¹ Ando, K.²

56
- 33845562410
- M. Terada, M. Nakano, H. Ube, J. Am. Chem. Soc. 2006, 128, 16044-16045
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 16044-16045
- Terada, M.¹ Nakano, M.² Ube, H.³

57
- 67649382042
- M. Nakano, M. Terada, Synlett 2009, 1670-1674
- (2009) Synlett , pp. 1670-1674
- Nakano, M.¹ Terada, M.²

58
- 72149085696
- M. Terada, D. Tsushima, M. Nakano, Adv. Synth. Catal. 2009, 351, 2817-2821
- (2009) Adv. Synth. Catal. , vol.351 , pp. 2817-2821
- Terada, M.¹ Tsushima, D.² Nakano, M.³

59
- 67649647843
- For a personal research account, see
- H. Ube, M. Terada, Bioorg. Med. Chem. Lett. 2009, 19, 3895-3898. For a personal research account, see
- (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 3895-3898
- Ube, H.¹ Terada, M.²

60
- 79551538268
- M. Terada, J. Synth. Org. Chem. Jpn. 2010, 68, 1159-1168.
- (2010) J. Synth. Org. Chem. Jpn. , vol.68 , pp. 1159-1168
- Terada, M.¹

61
- 0037006233
- For reviews of chiral guanidine catalysts, see: (a) T. Ishikawa, T. Isobe, Chem. Eur. J. 2002, 8, 552-557
- (2002) Chem. Eur. J. , vol.8 , pp. 552-557
- Ishikawa, T.¹ Isobe, T.²

62
- 33644922031
- T. Ishikawa, T. Kumamoto, Synthesis 2006, 737-752
- (2006) Synthesis , pp. 737-752
- Ishikawa, T.¹ Kumamoto, T.²

63
- 66149095568
- D. Leow, C.-H. Tan, Chem. Asian J. 2009, 4, 488-507.
- (2009) Chem. Asian J. , vol.4 , pp. 488-507
- Leow, D.¹ Tan, C.-H.²

64
- 33746929105
- M. Hatano, S. Suzuki, K. Ishihara, J. Am. Chem. Soc. 2006, 128, 9998-9999.
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 9998-9999
- Hatano, M.¹ Suzuki, S.² Ishihara, K.³

65
- 0033564990
- E. J. Corey, M. J. Grogan, Org. Lett. 1999, 1, 157-160
- (1999) Org. Lett. , vol.1 , pp. 157-160
- Corey, E.J.¹ Grogan, M.J.²

66
- 70349534248
- Z. Jiang, Y. Pan, Y. Zhao, T. Ma, R. Lee, Y. Yang, K.-W. Huang, M. W. Wong, C.-H. Tan, Angew. Chem. 2009, 121, 3681-3685
- (2009) Angew. Chem. , vol.121 , pp. 3681-3685
- Jiang, Z.¹ Pan, Y.² Zhao, Y.³ Ma, T.⁴ Lee, R.⁵ Yang, Y.⁶ Huang, K.-W.⁷ Wong, M.W.⁸ Tan, C.-H.⁹

67
- 70349769686
- Angew. Chem. Int. Ed. 2009, 48, 3627-3631.
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 3627-3631

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