SCOPUS 정보 검색 플랫폼

Volumn 10, Issue 25, 2012, Pages 4839-4843

Asymmetric Michael addition of boronic acids to a γ-hydroxy-α, β-unsaturated aldehyde catalyzed by resin-supported peptide

(3) Akagawa, Kengo a Sugiyama, Masahide a Kudo, Kazuaki a

a INSTITUTE OF INDUSTRIAL SCIENCE (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALDEHYDES; PEPTIDES; RESINS; SPECTROSCOPIC ANALYSIS;

BORONIC ACID; CATALYTIC ABILITY; MICHAEL ADDITIONS; SECONDARY STRUCTURES; SPECTRAL STUDIES; UNSATURATED ALDEHYDES;

UNSATURATED POLYMERS;

EID: 84862227134 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/c2ob25431j Document Type: Article

Times cited : (23)

References (73)

1
- 38349112828
- E. A. C. Davie S. M. Mennen Y. Xu S. J. Miller Chem. Rev. 2007 107 5759
- (2007) Chem. Rev. , vol.107 , pp. 5759
- Davie, E.A.C.¹ Mennen, S.M.² Xu, Y.³ Miller, S.J.⁴

2
- 80155209744
- For recent selected examples of organocatalytic reactions with peptides, see
- H. Wennemers Chem. Commun. 2011 47 12036
- (2011) Chem. Commun. , vol.47 , pp. 12036
- Wennemers, H.¹

3
- 42149137458
- V. D'Elia H. Zwicknagl O. Reiser J. Org. Chem. 2008 73 3262
- (2008) J. Org. Chem. , vol.73 , pp. 3262
- D'Elia, V.¹ Zwicknagl, H.² Reiser, O.³

4
- 42649098597
- M. Wiesner J. D. Revell S. Tonazzi H. Wennemers J. Am. Chem. Soc. 2008 130 5610
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 5610
- Wiesner, M.¹ Revell, J.D.² Tonazzi, S.³ Wennemers, H.⁴

5
- 57149086873
- C. A. Lewis J. L. Gustafson A. Chiu J. Balsells D. Pollard J. Murry R. A. Reamer K. B. Hansen S. J. Miller J. Am. Chem. Soc. 2008 130 16358
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 16358
- Lewis, C.A.¹ Gustafson, J.L.² Chiu, A.³ Balsells, J.⁴ Pollard, D.⁵ Murry, J.⁶ Reamer, R.A.⁷ Hansen, K.B.⁸ Miller, S.J.⁹

6
- 51649106845
- C. E. Müller L. Wanka K. Jewell P. R. Schreiner Angew. Chem., Int. Ed. 2008 47 6180
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 6180
- Müller, C.E.¹ Wanka, L.² Jewell, K.³ Schreiner, P.R.⁴

7
- 70350461493
- K. W. Fiori A. L. A. Puchlopek S. J. Miller Nat. Chem. 2009 1 630
- (2009) Nat. Chem. , vol.1 , pp. 630
- Fiori, K.W.¹ Puchlopek, A.L.A.² Miller, S.J.³

8
- 67649573965
- F.-C. Wu C.-S. Da Z.-X. Du Q.-P. Guo W.-P. Li L. Yi Y.-N. Jia X. Ma J. Org. Chem. 2009 74 4812
- (2009) J. Org. Chem. , vol.74 , pp. 4812
- Wu, F.-C.¹ Da, C.-S.² Du, Z.-X.³ Guo, Q.-P.⁴ Li, W.-P.⁵ Yi, L.⁶ Jia, Y.-N.⁷ Ma, X.⁸

9
- 70149092525
- B. J. Cowen L. B. Saunders S. J. Miller J. Am. Chem. Soc. 2009 131 6105
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 6105
- Cowen, B.J.¹ Saunders, L.B.² Miller, S.J.³

10
- 77953243317
- J. L. Gustafson D. Lim S. J. Miller Science 2010 328 1251
- (2010) Science , vol.328 , pp. 1251
- Gustafson, J.L.¹ Lim, D.² Miller, S.J.³

11
- 74849117325
- M. Wiesner G. Upert G. Angelici H. Wennemers J. Am. Chem. Soc. 2010 132 6
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 6
- Wiesner, M.¹ Upert, G.² Angelici, G.³ Wennemers, H.⁴

12
- 77950392067
- B. S. Fowler P. J. Mikochik S. J. Miller J. Am. Chem. Soc. 2010 132 2870
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 2870
- Fowler, B.S.¹ Mikochik, P.J.² Miller, S.J.³

13
- 79955551700
- P. Chen J. Qu J. Org. Chem. 2011 76 2994
- (2011) J. Org. Chem. , vol.76 , pp. 2994
- Chen, P.¹ Qu, J.²

14
- 79958805953
- F. Kolundzic M. N. Noshi M. Tjandra M. Movassaghi S. J. Miller J. Am. Chem. Soc. 2011 133 9104
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 9104
- Kolundzic, F.¹ Noshi, M.N.² Tjandra, M.³ Movassaghi, M.⁴ Miller, S.J.⁵

15
- 79958233596
- C. E. Müller R. Hrdina R. C. Wende P. R. Schreiner Chem.-Eur. J. 2011 17 6309
- (2011) Chem.-Eur. J. , vol.17 , pp. 6309
- Müller, C.E.¹ Hrdina, R.² Wende, R.C.³ Schreiner, P.R.⁴

16
- 80051775130
- G. Rulli N. Duangdee K. Baer W. Hummel A. Berkessel H. Gröger Angew. Chem., Int. Ed. 2011 50 7944
- (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 7944
- Rulli, G.¹ Duangdee, N.² Baer, K.³ Hummel, W.⁴ Berkessel, A.⁵ Gröger, H.⁶

17
- 35549002267
- For selected reviews of organocatalytic reactions, see
- T. Kawabata W. Muramatsu T. Nishio T. Shibata H. Schedel J. Am. Chem. Soc. 2007 129 12890
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 12890
- Kawabata, T.¹ Muramatsu, W.² Nishio, T.³ Shibata, T.⁴ Schedel, H.⁵

18
- 38349178582
- A. Erkkilä I. Majander P. M. Pihko Chem. Rev. 2007 107 5416
- (2007) Chem. Rev. , vol.107 , pp. 5416
- Erkkilä, A.¹ Majander, I.² Pihko, P.M.³

19
- 38349100690
- S. Mukherjee J. W. Yang S. Hoffmann B. List Chem. Rev. 2007 107 5471
- (2007) Chem. Rev. , vol.107 , pp. 5471
- Mukherjee, S.¹ Yang, J.W.² Hoffmann, S.³ List, B.⁴

20
- 34547623607
- H. Pellissier Tetrahedron 2007 63 9267
- (2007) Tetrahedron , vol.63 , pp. 9267
- Pellissier, H.¹

21
- 33847623075
- D. Almaşi D. A. Alonso C. Nájera Tetrahedron: Asymmetry 2007 18 299
- (2007) Tetrahedron: Asymmetry , vol.18 , pp. 299
- Almaşi, D.¹ Alonso, D.A.² Nájera, C.³

22
- 48849094479
- A. Dondoni A. Massi Angew. Chem., Int. Ed. 2008 47 4638
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 4638
- Dondoni, A.¹ Massi, A.²

23
- 53549121402
- For selected examples of relatively long peptide catalysts, see
- P. Melchiorre M. Marigo A. Carlone G. Bartoli Angew. Chem., Int. Ed. 2008 47 6138
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 6138
- Melchiorre, P.¹ Marigo, M.² Carlone, A.³ Bartoli, G.⁴

24
- 0034807976
- G. T. Copeland S. J. Miller J. Am. Chem. Soc. 2001 123 6496
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 6496
- Copeland, G.T.¹ Miller, S.J.²

25
- 33750437400
- M. M. Vasbinder J. E. Imbriglio S. J. Miller Tetrahedron 2006 62 11450
- (2006) Tetrahedron , vol.62 , pp. 11450
- Vasbinder, M.M.¹ Imbriglio, J.E.² Miller, S.J.³

26
- 41149131795
- M. Sánchez-Roselló A. L. A. Puchlopek A. J. Morgan S. J. Miller J. Org. Chem. 2008 73 1774
- (2008) J. Org. Chem. , vol.73 , pp. 1774
- Sánchez-Roselló, M.¹ Puchlopek, A.L.A.² Morgan, A.J.³ Miller, S.J.⁴

27
- 70349909688
- D. Coquière J. Bos J. Beld G. Roelfes Angew. Chem., Int. Ed. 2009 48 5159
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 5159
- Coquière, D.¹ Bos, J.² Beld, J.³ Roelfes, G.⁴

28
- 77955784263
- R. Sambasivan Z. T. Ball J. Am. Chem. Soc. 2010 132 9289
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 9289
- Sambasivan, R.¹ Ball, Z.T.²

29
- 47049117184
- K. Akagawa H. Akabane S. Sakamoto K. Kudo Org. Lett. 2008 10 2035
- (2008) Org. Lett. , vol.10 , pp. 2035
- Akagawa, K.¹ Akabane, H.² Sakamoto, S.³ Kudo, K.⁴

30
- 63249132986
- K. Akagawa H. Akabane S. Sakamoto K. Kudo Tetrahedron: Asymmetry 2009 20 461
- (2009) Tetrahedron: Asymmetry , vol.20 , pp. 461
- Akagawa, K.¹ Akabane, H.² Sakamoto, S.³ Kudo, K.⁴

31
- 68749105801
- K. Akagawa T. Yamashita S. Sakamoto K. Kudo Tetrahedron Lett. 2009 50 5602
- (2009) Tetrahedron Lett. , vol.50 , pp. 5602
- Akagawa, K.¹ Yamashita, T.² Sakamoto, S.³ Kudo, K.⁴

32
- 77951194201
- K. Akagawa T. Fujiwara S. Sakamoto K. Kudo Org. Lett. 2010 12 1804
- (2010) Org. Lett. , vol.12 , pp. 1804
- Akagawa, K.¹ Fujiwara, T.² Sakamoto, S.³ Kudo, K.⁴

33
- 77958460966
- K. Akagawa T. Fujiwara S. Sakamoto K. Kudo Chem. Commun. 2010 46 8040
- (2010) Chem. Commun. , vol.46 , pp. 8040
- Akagawa, K.¹ Fujiwara, T.² Sakamoto, S.³ Kudo, K.⁴

34
- 79959693358
- K. Akagawa K. Kudo Org. Lett. 2011 13 3498
- (2011) Org. Lett. , vol.13 , pp. 3498
- Akagawa, K.¹ Kudo, K.²

35
- 79955462698
- K. Akagawa K. Kudo Adv. Synth. Catal. 2011 353 843
- (2011) Adv. Synth. Catal. , vol.353 , pp. 843
- Akagawa, K.¹ Kudo, K.²

36
- 0000089981
- G. T. Copeland E. R. Jarvo S. J. Miller J. Org. Chem. 1998 63 6784
- (1998) J. Org. Chem. , vol.63 , pp. 6784
- Copeland, G.T.¹ Jarvo, E.R.² Miller, S.J.³

37
- 1242307810
- S. Aravinda V. V. Harini N. Shamala C. Das P. Balaram Biochemistry 2004 43 1832
- (2004) Biochemistry , vol.43 , pp. 1832
- Aravinda, S.¹ Harini, V.V.² Shamala, N.³ Das, C.⁴ Balaram, P.⁵

38
- 4143141139
- S. J. Miller Acc. Chem. Res. 2004 37 601
- (2004) Acc. Chem. Res. , vol.37 , pp. 601
- Miller, S.J.¹

39
- 33644599749
- Uozumi et al. have demonstrated that the PEG-PS-resin-support is effective for transition-metal-catalyzed reactions in water. For examples, see
- J. T. Blank S. J. Miller Pept Sci. 2006 84 38
- (2006) Pept Sci. , vol.84 , pp. 38
- Blank, J.T.¹ Miller, S.J.²

40
- 58149195436
- Y. Uozumi Bull. Chem. Soc. Jpn. 2008 81 1183
- (2008) Bull. Chem. Soc. Jpn. , vol.81 , pp. 1183
- Uozumi, Y.¹

41
- 70349786291
- Y. Uozumi Y. Matsuura T. Arakawa Y. M. A. Yamada Angew. Chem., Int. Ed. 2009 48 2708
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 2708
- Uozumi, Y.¹ Matsuura, Y.² Arakawa, T.³ Yamada, Y.M.A.⁴

42
- 73149083510
- T. Suzuka Y. Okada K. Ooshiro Y. Uozumi Tetrahedron 2010 66 1064
- (2010) Tetrahedron , vol.66 , pp. 1064
- Suzuka, T.¹ Okada, Y.² Ooshiro, K.³ Uozumi, Y.⁴

43
- 77955203510
- Y. Hirai Y. Uozumi Chem.-Asian J. 2010 5 1788
- (2010) Chem.-Asian J. , vol.5 , pp. 1788
- Hirai, Y.¹ Uozumi, Y.²

44
- 50549097452
- S.-G. Kim Tetrahedron Lett. 2008 49 6148
- (2008) Tetrahedron Lett. , vol.49 , pp. 6148
- Kim, S.-G.¹

45
- 75849146761
- For examples of asymmetric Michael additions with organoboron compounds by organocatalysts, see
- S.-G. Kim Bull. Korean Chem. Soc. 2009 30 2519
- (2009) Bull. Korean Chem. Soc. , vol.30 , pp. 2519
- Kim, S.-G.¹

46
- 14944346820
- T. R. Wu J. M. Chong J. Am. Chem. Soc. 2005 127 3244
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 3244
- Wu, T.R.¹ Chong, J.M.²

47
- 34247547062
- T. R. Wu J. M. Chong J. M. Chong J. Am. Chem. Soc. 2007 129 4908
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 4908
- Wu, T.R.¹ Chong, J.M.² Chong, J.M.³

48
- 37849041680
- S. Lee D. W. C. MacMillan J. Am. Chem. Soc. 2007 129 15438
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 15438
- Lee, S.¹ MacMillan, D.W.C.²

49
- 66149179009
- T. Inokuma K. Takasu T. Sakaeda Y. Takemoto Org. Lett. 2009 11 2425
- (2009) Org. Lett. , vol.11 , pp. 2425
- Inokuma, T.¹ Takasu, K.² Sakaeda, T.³ Takemoto, Y.⁴

50
- 77957839988
- M. Sugiura M. Tokudomi M. Nakajima Chem. Commun. 2010 46 7799
- (2010) Chem. Commun. , vol.46 , pp. 7799
- Sugiura, M.¹ Tokudomi, M.² Nakajima, M.³

51
- 77956225442
- K.-S. Choi S.-G. Kim Tetrahedron Lett. 2010 51 5203
- (2010) Tetrahedron Lett. , vol.51 , pp. 5203
- Choi, K.-S.¹ Kim, S.-G.²

52
- 78650264634
- K.-S. Choi S.-G. Kim Synthesis 2010 3999
- (2010) Synthesis , pp. 3999
- Choi, K.-S.¹ Kim, S.-G.²

53
- 80052714730
- For other examples of organocatalyzed reactions with organoboronic acids, see
- B. J. Lundy S. Jansone-Popova J. A. May Org. Lett. 2011 13 4958
- (2011) Org. Lett. , vol.13 , pp. 4958
- Lundy, B.J.¹ Jansone-Popova, S.² May, J.A.³

54
- 33749514608
- S. Lou P. N. Moquist S. E. Schaus J. Am. Chem. Soc. 2006 128 12660
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 12660
- Lou, S.¹ Moquist, P.N.² Schaus, S.E.³

55
- 37049035131
- S. Lou P. N. Moquist S. E. Schaus J. Am. Chem. Soc. 2007 129 15398
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 15398
- Lou, S.¹ Moquist, P.N.² Schaus, S.E.³

56
- 44449092080
- S. Lou S. E. Schaus J. Am. Chem. Soc. 2008 130 6922
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 6922
- Lou, S.¹ Schaus, S.E.²

57
- 70349939560
- J. A. Bishop S. Lou S. E. Schaus Angew. Chem., Int. Ed. 2009 48 4337
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 4337
- Bishop, J.A.¹ Lou, S.² Schaus, S.E.³

58
- 70350588841
- D. S. Barnett P. N. Moquist S. E. Schaus Angew. Chem., Int. Ed. 2009 48 8679
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 8679
- Barnett, D.S.¹ Moquist, P.N.² Schaus, S.E.³

59
- 34249793225
- Y. Yamaoka H. Miyabe Y. Takemoto J. Am. Chem. Soc. 2007 129 6686
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 6686
- Yamaoka, Y.¹ Miyabe, H.² Takemoto, Y.³

60
- 80155150860
- For selected reviews of metal-catalyzed Michael reactions with organoboron reagents, see
- T. Inokuma Y. Suzuki T. Sakaeda Y. Takemoto Chem.-Asian J. 2011 6 2902
- (2011) Chem.-Asian J. , vol.6 , pp. 2902
- Inokuma, T.¹ Suzuki, Y.² Sakaeda, T.³ Takemoto, Y.⁴

61
- 0041738169
- T. Hayashi K. Yamasaki Chem. Rev. 2003 103 2829
- (2003) Chem. Rev. , vol.103 , pp. 2829
- Hayashi, T.¹ Yamasaki, K.²

62
- 58149289357
- N. Miyaura Bull. Chem. Soc. Jpn. 2008 81 1535
- (2008) Bull. Chem. Soc. Jpn. , vol.81 , pp. 1535
- Miyaura, N.¹

63
- 68949151956
- N. Miyaura Synlett 2009 2039
- (2009) Synlett , pp. 2039
- Miyaura, N.¹

64
- 77952748638
- F. C. Pigge Synthesis 2010 1745
- (2010) Synthesis , pp. 1745
- Pigge, F.C.¹

65
- 80051581714
- The diastereomeric ratio of the lactol product was about 6:4. In all cases in Table 1, diastereoselectivity was almost the same Córdova et al. reported that a dialanyl peptide effectively catalyzes the asymmetric Michael addition of nitroolefins to ketones
- C. S. Marques A. J. Burke ChemCatChem 2011 3 635
- (2011) ChemCatChem , vol.3 , pp. 635
- Marques, C.S.¹ Burke, A.J.²

66
- 33645909878
- The concentration of the peptides was 0.5 mM. In the case of the sequence of Pro-d-Pro-Aib-(Ala)5, the solubility of the peptide was not enough. This might be the cause of somewhat smaller molar ellipticity than those of the peptides with (Ala)n (n = 2 to 4)
- Y. Xu W. Zou H. Sundén I. Ibrahem A. Córdova Adv. Synth. Catal. 2006 348 418
- (2006) Adv. Synth. Catal. , vol.348 , pp. 418
- Xu, Y.¹ Zou, W.² Sundén, H.³ Ibrahem, I.⁴ Córdova, A.⁵

67
- 0346837918
- S. R. Raghothama S. K. Awasthi P. Balaram J. Chem. Soc., Perkin Trans. 2 1998 137
- (1998) J. Chem. Soc., Perkin Trans. 2 , pp. 137
- Raghothama, S.R.¹ Awasthi, S.K.² Balaram, P.³

68
- 0035130373
- C. Das G. A. Naganagowda I. L. Karle P. Balaram Biopolymers 2001 58 335
- (2001) Biopolymers , vol.58 , pp. 335
- Das, C.¹ Naganagowda, G.A.² Karle, I.L.³ Balaram, P.⁴

69
- 0037131459
- S. Aravinda N. Shamala R. Rajkishore H. N. Gopi P. Balaram Angew. Chem., Int. Ed. 2002 41 3863
- (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 3863
- Aravinda, S.¹ Shamala, N.² Rajkishore, R.³ Gopi, H.N.⁴ Balaram, P.⁵

70
- 80055072261
- M. G. Bomar B. Song P. Kibler K. Kodukula A. K. Galande Org. Lett. 2011 13 5878
- (2011) Org. Lett. , vol.13 , pp. 5878
- Bomar, M.G.¹ Song, B.² Kibler, P.³ Kodukula, K.⁴ Galande, A.K.⁵

71
- 34248383247
- R. Rai S. Raghothama R. Sridharan P. Balaram Pept. Sci. 2007 88 350
- (2007) Pept. Sci. , vol.88 , pp. 350
- Rai, R.¹ Raghothama, S.² Sridharan, R.³ Balaram, P.⁴

72
- 0029931671
- T. S. Haque J. C. Little S. H. Gellman J. Am. Chem. Soc. 1996 118 6975
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 6975
- Haque, T.S.¹ Little, J.C.² Gellman, S.H.³

73
- 84860726436
- K. Akagawa R. Suzuki K. Kudo Adv. Synth. Catal. 2012 354 1280
- (2012) Adv. Synth. Catal. , vol.354 , pp. 1280
- Akagawa, K.¹ Suzuki, R.² Kudo, K.³

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