SCOPUS 정보 검색 플랫폼

Chemical Communications

Volumn , Issue 26, 2008, Pages 3043-3045

Asymmetric autocatalytic Mannich reaction in the presence of water and its implication in prebiotic chemistry

(2) Amedjkouh, Mohamed a Brandberg, Maria a

a UNIVERSITY OF GOTHENBURG (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

PREBIOTIC AGENT; WATER;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; MANNICH REACTION; REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY;

EID: 46149091526 PISSN: 13597345 EISSN: None Source Type: Journal
DOI: 10.1039/b804142n Document Type: Article

Times cited : (47)

References (44)

1
- 0005540903
- F. C. Frank Biochim. Biophys. Acta 1953 11 459
- (1953) Biochim. Biophys. Acta , vol.11 , pp. 459
- Frank, F.C.¹

2
- 0014447324
- Oxford University Press, Oxford
- M. Calvin, Chemical Evolution, Oxford University Press, Oxford, 1969
- (1969) Chemical Evolution
- Calvin, M.¹

3
- 2642647764
- A. H. Alberts H. Wynberg J. Am. Chem. Soc. 1989 111 7265
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 7265
- Alberts, A.H.¹ Wynberg, H.²

4
- 37049089869
- A. H. Alberts H. Wynberg J. Chem. Soc., Chem. Commun. 1990 453
- (1990) J. Chem. Soc., Chem. Commun. , pp. 453
- Alberts, A.H.¹ Wynberg, H.²

5
- 33751499922
- H. Danda H. Nishikawa K. Otaka J. Org. Chem. 1991 56 6740
- (1991) J. Org. Chem. , vol.56 , pp. 6740
- Danda, H.¹ Nishikawa, H.² Otaka, K.³

6
- 4544276855
- S. P. Mathew H. Iwamura D. G. Blackmond Angew. Chem., Int. Ed. 2004 43 3317
- (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 3317
- Mathew, S.P.¹ Iwamura, H.² Blackmond, D.G.³

7
- 4644348576
- H. Iwamura S. P. Mathew D. G. Blackmond J. Am. Chem. Soc. 2004 126 11770
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 11770
- Iwamura, H.¹ Mathew, S.P.² Blackmond, D.G.³

8
- 11444256330
- H. Iwamura D. H. Wells, Jr S. P. Mathew M. Klussmann A. Armstrong D. G. Blackmond J. Am. Chem. Soc. 2004 126 16312
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 16312
- Iwamura, H.¹ Wells Jr., D.H.² Mathew, S.P.³ Klussmann, M.⁴ Armstrong, A.⁵ Blackmond, D.G.⁶

9
- 0039842613
- M. Szlosek B. Figadère Angew. Chem., Int. Ed. 2000 39 1799
- (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 1799
- Szlosek, M.¹ Figadère, B.²

10
- 0000066091
- F. Rebiere O. Riant H. B. Kagan Tetrahedron: Asymmetry 1990 1 199
- (1990) Tetrahedron: Asymmetry , vol.1 , pp. 199
- Rebiere, F.¹ Riant, O.² Kagan, H.B.³

11
- 0030669121
- For the first publications, see:
- D. P. Heller D. R. Goldberg W. D. Wulff J. Am. Chem. Soc. 1997 119 10551
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 10551
- Heller, D.P.¹ Goldberg, D.R.² Wulff, W.D.³

12
- 37049082787
- K. Soai S. Niwa H. Hori J. Chem. Soc., Chem. Commun. 1990 982
- (1990) J. Chem. Soc., Chem. Commun. , pp. 982
- Soai, K.¹ Niwa, S.² Hori, H.³

13
- 0029559848
- K. Soai T. Shibata H. Morioka K. Choji Nature 1995 378 767
- (1995) Nature , vol.378 , pp. 767
- Soai, K.¹ Shibata, T.² Morioka, H.³ Choji, K.⁴

14
- 0002814769
- T. Shibata K. Choji T. Hayase Y. Aizu K. Soai Chem. Commun. 1996 1235
- (1996) Chem. Commun. , pp. 1235
- Shibata, T.¹ Choji, K.² Hayase, T.³ Aizu, Y.⁴ Soai, K.⁵

15
- 0000235486
- for a recent review, see:
- T. Shibata H. Morioka T. Hayase K. Choji K. Soai J. Am. Chem. Soc. 1996 118 471
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 471
- Shibata, T.¹ Morioka, H.² Hayase, T.³ Choji, K.⁴ Soai, K.⁵

16
- 33745345824
- K. Soai T. Kawasaki Chirality 2006 18 469
- (2006) Chirality , vol.18 , pp. 469
- Soai, K.¹ Kawasaki, T.²

17
- 0028306647
- D. Sievers G. von Kiedrowski Nature 1994 369 221
- (1994) Nature , vol.369 , pp. 221
- Sievers, D.¹ Von Kiedrowski, G.²

18
- 17044437071
- V. K. Aggarwal S. Y. Fulford G. C. Lloyd-Jones Angew. Chem., Int. Ed. 2005 44 1706
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 1706
- Aggarwal, V.K.¹ Fulford, S.Y.² Lloyd-Jones, G.C.³

19
- 5144223058
- For reviews, see:
- H. Fujisawa T. Nakagawa T. Mukaiyama Adv. Synth. Catal. 2004 346 1241
- (2004) Adv. Synth. Catal. , vol.346 , pp. 1241
- Fujisawa, H.¹ Nakagawa, T.² Mukaiyama, T.³

20
- 0037043180
- B. List Tetrahedron 2002 58 5573
- (2002) Tetrahedron , vol.58 , pp. 5573
- List, B.¹

21
- 33646468489
- M. S. Taylor E. N. Jacobsen Angew. Chem., Int. Ed. 2006 45 1520
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 1520
- Taylor, M.S.¹ Jacobsen, E.N.²

22
- 6044269452
- P. I. Dalko L. Moisan Angew. Chem., Int. Ed. 2004 43 5138
- (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 5138
- Dalko, P.I.¹ Moisan, L.²

23
- 15244343428
- J. Seayad B. List Org. Biomol. Chem. 2005 3 719
- (2005) Org. Biomol. Chem. , vol.3 , pp. 719
- Seayad, J.¹ List, B.²

24
- 5144229459
- W. Notz S.-I. Watanabe N. S. Chowdari G. Zhong J. M. Betancort F. Tanaka C. F. Barbas III Adv. Synth. Catal. 2004 356 1131
- (2004) Adv. Synth. Catal. , vol.356 , pp. 1131
- Notz, W.¹ Watanabe, S.-I.² Chowdari, N.S.³ Zhong, G.⁴ Betancort, J.M.⁵ Tanaka, F.⁶ Barbas III, C.F.⁷

25
- 11844253794
- A. J. A. Cobb D. M. Shaw D. A. Longbottom J. B. Gold S. V. Ley Org. Biomol. Chem. 2005 3 84
- (2005) Org. Biomol. Chem. , vol.3 , pp. 84
- Cobb, A.J.A.¹ Shaw, D.M.² Longbottom, D.A.³ Gold, J.B.⁴ Ley, S.V.⁵

26
- 33746606463
- H. Zhang M. Mifsud F. Tanaka C. F. Barbas III J. Am. Chem. Soc. 2006 128 9630
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 9630
- Zhang, H.¹ Mifsud, M.² Tanaka, F.³ Barbas III, C.F.⁴

27
- 33846529045
- M. Mauksch S. B. Tsogoeva I. Martynova S.-W. Wei Angew. Chem., Int. Ed. 2007 46 393
- (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 393
- Mauksch, M.¹ Tsogoeva, S.B.² Martynova, I.³ Wei, S.-W.⁴

28
- 38449111671
- Anti- 3 was assigned by comparison of spectroscopic data with those reported in ref. 10c
- M. Mauksch S. B. Tsogoeva S.-W. Wei I. Martynova Chirality 2007 19 816
- (2007) Chirality , vol.19 , pp. 816
- Mauksch, M.¹ Tsogoeva, S.B.² Wei, S.-W.³ Martynova, I.⁴

29
- 46149104629
- All reactions in aqueous media were performed in triplicate
- All reactions in aqueous media were performed in triplicate

30
- 31444456557
- N. Mase Y. Nakai N. Ohara H. Yoda K. Takabe F. Tanaka C. F. Barbas III J. Am. Chem. Soc. 2006 128 734
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 734
- Mase, N.¹ Nakai, Y.² Ohara, N.³ Yoda, H.⁴ Takabe, K.⁵ Tanaka, F.⁶ Barbas III, C.F.⁷

31
- 32044463187
- Y. Hayashi T. Sumiya J. Takahashi H. Gotoh T. Urushima M. Shoji Angew. Chem., Int. Ed. 2006 45 958
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 958
- Hayashi, Y.¹ Sumiya, T.² Takahashi, J.³ Gotoh, H.⁴ Urushima, T.⁵ Shoji, M.⁶

32
- 33646142092
- N. Mase K. Watanabe H. Yoda K. Takabe F. Tanaka C. F. Barbas III J. Am. Chem. Soc. 2006 128 4966
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 4966
- Mase, N.¹ Watanabe, K.² Yoda, H.³ Takabe, K.⁴ Tanaka, F.⁵ Barbas III, C.F.⁶

33
- 33847638971
- M. Amedjkouh Tetrahedron: Asymmetry 2007 18 390
- (2007) Tetrahedron: Asymmetry , vol.18 , pp. 390
- Amedjkouh, M.¹

34
- 46149125639
- Similar conditions in the presence of anionic surfactant such as sodium dodecylsulfate (SDS) produced only racemates For example reaction in NaCl (3.0 M) produced the syn- 3 with 44% ee. For discussion on the effects of added salts and their concentrations on reactivity in water see:
- Similar conditions in the presence of anionic surfactant such as sodium dodecylsulfate (SDS) produced only racemates

35
- 3242699566
- NMR analysis of the reaction mixture showed a significant equilibrium concentration of the imine 2
- R. Breslow Acc. Chem. Res. 2004 37 471
- (2004) Acc. Chem. Res. , vol.37 , pp. 471
- Breslow, R.¹

36
- 0032538773
- C. Girard H. B. Kagan Angew. Chem., Int. Ed. 1998 37 2922
- (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2922
- Girard, C.¹ Kagan, H.B.²

37
- 0000417261
- For the Franck model see ref. 1a
- D. G. Blackmond Adv. Synth. Catal. 2002 344 156
- (2002) Adv. Synth. Catal. , vol.344 , pp. 156
- Blackmond, D.G.¹

38
- 46149113578
- One referee suggested the use of ethyl glyoxylate in excess to trap the p-anisidine. However, we were unable to observe any significant change in the selectivity The syn- 3 with 98% ee was let to stand in water at rt without any alteration of er or dr after three days. However, upon addition of p-anisidine, we observed isomerisation of syn- 3 into enantiopoor anti- 3, however, we were not able to assign the enantiomers
- One referee suggested the use of ethyl glyoxylate in excess to trap the p-anisidine. However, we were unable to observe any significant change in the selectivity

39
- 46149119752
- a = 6.95) isomerization of the anti-Mannich into syn-Mannich as reported by Barbas et al.
- a = 6.95) isomerization of the anti-Mannich into syn-Mannich as reported by Barbas et al.

40
- 31944446866
- See supporting information in ref. 10c. For imidazole isomerisation of aldols see:
- S. Mitsumori H. Zhang P. H.-Y. Cheong K. N. Houk F. Tanaka C. F. Barbas III J. Am. Chem. Soc. 2006 128 1040
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 1040
- Mitsumori, S.¹ Zhang, H.² Cheong, P.H.-Y.³ Houk, K.N.⁴ Tanaka, F.⁵ Barbas III, C.F.⁶

41
- 3042698496
- A preliminary study showed that anti- 3, isolated from the reaction in DMF, catalyzed the formation of anti: syn- 3 (10: 9) mixture with no measurable selectivity. Work is currently under way to assess the catalytic effect of the enantiomerically pure anti- 3
- D. E. Ward M. Sales P. J. Sasmal J. Org. Chem. 2004 69 4808
- (2004) J. Org. Chem. , vol.69 , pp. 4808
- Ward, D.E.¹ Sales, M.² Sasmal, P.J.³

42
- 0030583528
- K. Soai Y. Inoue T. Takahashi T. Shibata Tetrahedron 1996 52 13355
- (1996) Tetrahedron , vol.52 , pp. 13355
- Soai, K.¹ Inoue, Y.² Takahashi, T.³ Shibata, T.⁴

43
- 20344388819
- S. Narayan J. Muldoon M. G. Finn V. V. Fokin H. C. Kolb K. B. Sharpless Angew. Chem., Int. Ed. 2005 44 3275
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 3275
- Narayan, S.¹ Muldoon, J.² Finn, M.G.³ Fokin, V.V.⁴ Kolb, H.C.⁵ Sharpless, K.B.⁶

44
- 0041818406
- See also ref. 16
- S. Otto J. B. F. N. Engberts Org. Biomol. Chem. 2003 1 2809
- (2003) Org. Biomol. Chem. , vol.1 , pp. 2809
- Otto, S.¹ Engberts, J.B.F.N.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.