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Organic and Biomolecular Chemistry

Volumn 9, Issue 14, 2011, Pages 5079-5085

First asymmetric cascade reaction catalysed by chiral primary aminoalcohols

(5) Arróniz, Carlos a Escolano, Carmen a Luque, F Javier a Bosch, Joan a Amat, Mercedes a

a UNIVERSITY OF BARCELONA (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,2-AMINOALCOHOLS; AMINO ALCOHOLS; CASCADE REACTIONS; CATALYSE; CATALYTIC ACTIVATION; CHIRAL SPECIES; COCATALYST; CYCLOHEXANONES; MICHAEL-ALDOL REACTIONS; ORGANOCATALYSTS; PRIMARY AMINES; REACTION MECHANISM; SECONDARY AMINES; THEORETICAL STUDY;

CONDENSATION REACTIONS;

AMINES;

AMINOALCOHOL; CYCLOHEXANONE; CYCLOHEXANONE DERIVATIVE; DIAMINE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; QUANTUM THEORY; STEREOISOMERISM; SYNTHESIS;

AMINO ALCOHOLS; CATALYSIS; CYCLOHEXANONES; DIAMINES; MOLECULAR STRUCTURE; QUANTUM THEORY; STEREOISOMERISM;

EID: 79959811767 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/c1ob05400g Document Type: Article

Times cited : (16)

References (49)

1
- 47749122232
- Wiley-VCH, Weinheim
- A. Berkessel, H. Gröger, Asymmetric Organocatalysis, Wiley-VCH, Weinheim, 2005
- (2005) Asymmetric Organocatalysis
- Berkessel, A.¹ Gröger, H.²

2
- 55049138759
- Wiley-VCH, Weinheim
- P. I Dalko, Enantioselective Organocatalysis, Wiley-VCH, Weinheim, 2007
- (2007) Enantioselective Organocatalysis
- Dalko, P.I.¹

3
- 78649322702
- RCS Publishing
- H. Pellissier, Recent Developments in Asymmetric Organocatalysis, RCS Publishing, 2010. For selected reviews, see:
- (2010) Recent Developments in Asymmetric Organocatalysis
- Pellissier, H.¹

4
- 27344444510
- Special Issue on Asymmetric Organocatalysis
- Special Issue on Asymmetric Organocatalysis:, Acc. Chem. Res., 2004, 37, (8)
- (2004) Acc. Chem. Res. , Issue.8

5
- 79959780552
- Special edition on organocatalysis
- Special edition on organocatalysis: Chem. Rev., 2007, 107
- (2007) Chem. Rev.

6
- 52149113820
- D. W. C. MacMillan Nature 2008 455 304 308
- (2008) Nature , vol.455 , pp. 304-308
- MacMillan, D.W.C.¹

7
- 69249088448
- S. Bertelsen K. A. Jørgensen Chem. Soc. Rev. 2009 38 2178 2189
- (2009) Chem. Soc. Rev. , vol.38 , pp. 2178-2189
- Bertelsen, S.¹ Jørgensen, K.A.²

8
- 33845766272
- M. J. Gaunt C. C. C. Johansson A. McNally N. T. Vo Drug Discov. Today 2007 12 8 27
- (2007) Drug Discov. Today , vol.12 , pp. 8-27
- Gaunt, M.J.¹ Johansson, C.C.C.² McNally, A.³ Vo, N.T.⁴

9
- 34250684250
- R. M. De Figueiredo M. Christmann Eur. J. Org. Chem. 2007 2575 2600
- (2007) Eur. J. Org. Chem. , pp. 2575-2600
- De Figueiredo, R.M.¹ Christmann, M.²

10
- 77954827954
- For selected reviews on asymmetric aminocatalysis, see:
- E. Marqués-López R. P. Herrera M. Christmann Nat. Prod. Rep. 2010 27 1138 1167
- (2010) Nat. Prod. Rep. , vol.27 , pp. 1138-1167
- Marqués-López, E.¹ Herrera, R.P.² Christmann, M.³

11
- 32844457119
- B. List Chem. Commun. 2006 819 824
- (2006) Chem. Commun. , pp. 819-824
- List, B.¹

12
- 53549121402
- P. Melchiore M. Marigo A. Carlone G. Bartoli Angew. Chem., Int. Ed. 2008 47 6138 6171
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 6138-6171
- Melchiore, P.¹ Marigo, M.² Carlone, A.³ Bartoli, G.⁴

13
- 77749298554
- For selected reviews on primary amine catalysis, see:
- B. List Angew. Chem., Int. Ed. 2010 49 1730 1734
- (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 1730-1734
- List, B.¹

14
- 43049134765
- F. Peng Z. Shao J. Mol. Catal. A: Chem. 2008 285 1 13
- (2008) J. Mol. Catal. A: Chem. , vol.285 , pp. 1-13
- Peng, F.¹ Shao, Z.²

15
- 78650119372
- L.-W. Wu Y. Lu Org. Biomol. Chem. 2008 6 2047 2053
- (2008) Org. Biomol. Chem. , vol.6 , pp. 2047-2053
- Wu, L.-W.¹ Lu, Y.²

16
- 67549137639
- L.-W. Xu J. Luo Y. Lu Chem. Commun. 2009 1807 1821
- (2009) Chem. Commun. , pp. 1807-1821
- Xu, L.-W.¹ Luo, J.² Lu, Y.³

17
- 49649083136
- Y.-C. Chen Synlett 2008 1919 1930
- (2008) Synlett , pp. 1919-1930
- Chen, Y.-C.¹

18
- 48349106907
- For reviews on organocatalytic domino/cascade reactions, see:
- G. Bartoli P. Melchiorre Synlett 2008 1759 1772
- (2008) Synlett , pp. 1759-1772
- Bartoli, G.¹ Melchiorre, P.²

19
- 33947198541
- D. Enders C. Grondal M. R. M. Hüttl Angew. Chem., Int. Ed. 2007 46 1570 1581
- (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 1570-1581
- Enders, D.¹ Grondal, C.² Hüttl, M.R.M.³

20
- 75749109355
- B. Westermann M. Ayaz S. S. van Berkel Angew. Chem., Int. Ed. 2010 49 846 849
- (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 846-849
- Westermann, B.¹ Ayaz, M.² Van Berkel, S.S.³

21
- 77649087999
- C. Grondal M. Jeanty D. Enders Nat. Chem. 2010 2 167 178
- (2010) Nat. Chem. , vol.2 , pp. 167-178
- Grondal, C.¹ Jeanty, M.² Enders, D.³

22
- 44949242294
- X. Yu W. Wang Org. Biomol. Chem. 2008 6 2037 2046
- (2008) Org. Biomol. Chem. , vol.6 , pp. 2037-2046
- Yu, X.¹ Wang, W.²

23
- 79959785040
- S. Vera P. Melchiore An. Quím. 2010 106 277 284
- (2010) An. Quím. , vol.106 , pp. 277-284
- Vera, S.¹ Melchiore, P.²

24
- 33750977591
- K. C. Nicolaou D. J. Edmonds P. G. Bulger Angew. Chem., Int. Ed. 2006 45 7134 7186
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 7134-7186
- Nicolaou, K.C.¹ Edmonds, D.J.² Bulger, P.G.³

25
- 70350519146
- For a review on 1,2-aminoalcohols as chiral auxiliaries in asymmetric synthesis, see:
- K. C. Nicolaou J. S. Chen Chem. Soc. Rev. 2009 38 2993 3009
- (2009) Chem. Soc. Rev. , vol.38 , pp. 2993-3009
- Nicolaou, K.C.¹ Chen, J.S.²

26
- 0038468227
- D. J. Ager I. Prakash D. R. Schaad Chem. Rev. 1996 96 835 875
- (1996) Chem. Rev. , vol.96 , pp. 835-875
- Ager, D.J.¹ Prakash, I.² Schaad, D.R.³

27
- 33751025895
- C. Escolano M. Amat J. Bosch Chem.-Eur. J. 2006 12 8198 8207
- (2006) Chem.-Eur. J. , vol.12 , pp. 8198-8207
- Escolano, C.¹ Amat, M.² Bosch, J.³

28
- 78651401179
- For a review on catalytic applications of nitrogen-containing ligands, including 1,2-aminoalcohols, see:
- M. Amat M. Pérez J. Bosch Synlett 2011 143 160
- (2011) Synlett , pp. 143-160
- Amat, M.¹ Pérez, M.² Bosch, J.³

29
- 0033714636
- For examples on the use of chiral primary aminoalcohols as metal-free organocatalysts, see:
- F. Fache E. Schultz M. L. Tommasino M. Lemaire Chem. Rev. 2000 100 2159 2232
- (2000) Chem. Rev. , vol.100 , pp. 2159-2232
- Fache, F.¹ Schultz, E.² Tommasino, M.L.³ Lemaire, M.⁴

30
- 38349176362
- A. V. Malkov M. A. Kabeshov M. Bella O. Kysilka D. A. Mayshev K. Pluháková P. Koovský Org. Lett. 2007 9 5473 5476
- (2007) Org. Lett. , vol.9 , pp. 5473-5476
- Malkov, A.V.¹ Kabeshov, M.A.² Bella, M.³ Kysilka, O.⁴ Mayshev, D.A.⁵ Pluháková, K.⁶ Koovský, P.⁷

31
- 53749108479
- A. Russo A. Lattanzi Eur. J. Org. Chem. 2008 2767 2773
- (2008) Eur. J. Org. Chem. , pp. 2767-2773
- Russo, A.¹ Lattanzi, A.²

32
- 70350159250
- T. E. Kristensen K. Vestli F. K. Hansen T. Hansen Eur. J. Org. Chem. 2009 5185 5191
- (2009) Eur. J. Org. Chem. , pp. 5185-5191
- Kristensen, T.E.¹ Vestli, K.² Hansen, F.K.³ Hansen, T.⁴

33
- 2342614099
- Recently, a novel oxazolidine has been used as an organocatalyst for the first time:
- N. Halland P. S. Aburel K. A. Jørgensen Angew. Chem., Int. Ed. 2004 43 1272 1277
- (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 1272-1277
- Halland, N.¹ Aburel, P.S.² Jørgensen, K.A.³

34
- 77953896626
- At shorter reaction times (3 days), a decrease in yield (21%) is observed, although the ee was higher (89%). The use of ethyl benzoylacetate instead of benzyl benzoylacetate as starting material with 2 as catalyst provided lower yield (61%) and ee (44%). Comparable results were previously reported by Jørgensen and coworkers (ref. 10)
- H. Nakano K. Osone M. Takeshita E. Kwon C. Seki H. Matsuyama N. Takano Y. Kohari Chem. Commun. 2010 46 4827 4829
- (2010) Chem. Commun. , vol.46 , pp. 4827-4829
- Nakano, H.¹ Osone, K.² Takeshita, M.³ Kwon, E.⁴ Seki, C.⁵ Matsuyama, H.⁶ Takano, N.⁷ Kohari, Y.⁸

35
- 0037195702
- N. Halland R. G. Hazell K. A. Jørgensen J. Org. Chem. 2002 67 8331 8338
- (2002) J. Org. Chem. , vol.67 , pp. 8331-8338
- Halland, N.¹ Hazell, R.G.² Jørgensen, K.A.³

36
- 0037429423
- N. Halland P. S. Aburel K. A. Jørgensen Angew. Chem., Int. Ed. 2003 42 661 665
- (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 661-665
- Halland, N.¹ Aburel, P.S.² Jørgensen, K.A.³

37
- 0242323633
- N. Halland T. Hansen K. A. Jørgensen Angew. Chem., Int. Ed. 2003 42 4955 4957
- (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 4955-4957
- Halland, N.¹ Hansen, T.² Jørgensen, K.A.³

38
- 5444266167
- A mechanism involving a diamine catalyst (diphenylethylenediamine), instead of the previously supposed imidazolidine catalyst, has been proposed:
- J. Pulkkinen P. S. Aburel N. Halland K. A. Jørgensen Adv. Synth. Catal. 2004 346 1077 1080
- (2004) Adv. Synth. Catal. , vol.346 , pp. 1077-1080
- Pulkkinen, J.¹ Aburel, P.S.² Halland, N.³ Jørgensen, K.A.⁴

39
- 33845262220
- H. Kim C. Yen P. Preston J. Chin Org. Lett. 2006 8 5239 5242
- (2006) Org. Lett. , vol.8 , pp. 5239-5242
- Kim, H.¹ Yen, C.² Preston, P.³ Chin, J.⁴

40
- 70349786290
- L.-Y. Wu G. Bencivenni M. Mancinelli A. Mazzanti G. Bartoli P. Melchiorre Angew. Chem., Int. Ed. 2009 48 7196 7199
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 7196-7199
- Wu, L.-Y.¹ Bencivenni, G.² Mancinelli, M.³ Mazzanti, A.⁴ Bartoli, G.⁵ Melchiorre, P.⁶

41
- 70349784950
- G. Bencivenni L.-Y. Wu A. Mazzanti B. Giannichi F. Pesciaioli M.-P. Song G. Bartoli P. Melchiorre Angew. Chem., Int. Ed. 2009 48 7200 7203
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 7200-7203
- Bencivenni, G.¹ Wu, L.-Y.² Mazzanti, A.³ Giannichi, B.⁴ Pesciaioli, F.⁵ Song, M.-P.⁶ Bartoli, G.⁷ Melchiorre, P.⁸

42
- 72449177404
- Y.-Q. Yang Z. Chai H.-F. Wang X.-K. Chen H.-F Cui C.-W. Zheng H. Xiao P. Li G. Zhao Chem.-Eur. J. 2009 15 13295 13298
- (2009) Chem.-Eur. J. , vol.15 , pp. 13295-13298
- Yang, Y.-Q.¹ Chai, Z.² Wang, H.-F.³ Chen, X.-K.⁴ Cui, H.-F.⁵ Zheng, C.-W.⁶ Xiao, H.⁷ Li, P.⁸ Zhao, G.⁹

43
- 73449145126
- H.-F. Cui Y.-Q. Yang Z. Chai P. Li C.-W. Zheng S.-Z. Zhu G. Zhao J. Org. Chem. 2010 75 117 122
- (2010) J. Org. Chem. , vol.75 , pp. 117-122
- Cui, H.-F.¹ Yang, Y.-Q.² Chai, Z.³ Li, P.⁴ Zheng, C.-W.⁵ Zhu, S.-Z.⁶ Zhao, G.⁷

44
- 0343520793
- A) would play a major role as catalyst. In a related case, a 1,4-cis heterocyclic diastereoisomer was shown to be more reactive than the trans isomer in an N-acylation process. This can be rationalized taking into account that substituents in trans relationship shield the nitrogen inhibiting a nucleophilic attack. For the related example, see:
- Y. Hirai T. Terada T. Yamazaki T. Momose J. Chem. Soc., Perkin Trans. 1 1992 509 516
- (1992) J. Chem. Soc., Perkin Trans. 1 , pp. 509-516
- Hirai, Y.¹ Terada, T.² Yamazaki, T.³ Momose, T.⁴

45
- 0001866555
- See also ref. 11
- W. Ando Y. Igarashi L. Huang Chem. Lett. 1987 1361 1364
- (1987) Chem. Lett. , pp. 1361-1364
- Ando, W.¹ Igarashi, Y.² Huang, L.³

46
- 0037060005
- C.-Q. Sun P. T. W. Cheng J. Stevenson T. Dejneka B. Brown T. C. Wang J. A. Robl M. A. Poss Tetrahedron Lett. 2002 43 1161 1164
- (2002) Tetrahedron Lett. , vol.43 , pp. 1161-1164
- Sun, C.-Q.¹ Cheng, P.T.W.² Stevenson, J.³ Dejneka, T.⁴ Brown, B.⁵ Wang, T.C.⁶ Robl, J.A.⁷ Poss, M.A.⁸

47
- 62349126517
- S. E. Howson L. E. N. Allan N. P. Chmel G. J. Clarkson R. Gorkum P. Scott Chem. Commun. 2009 1727 1729
- (2009) Chem. Commun. , pp. 1727-1729
- Howson, S.E.¹ Allan, L.E.N.² Chmel, N.P.³ Clarkson, G.J.⁴ Gorkum, R.⁵ Scott, P.⁶

48
- 0037184882
- S. M. Allin S. L. James M. R. J. Elsegood W. P. Martin J. Org. Chem. 2002 67 9464 9467
- (2002) J. Org. Chem. , vol.67 , pp. 9464-9467
- Allin, S.M.¹ James, S.L.² Elsegood, M.R.J.³ Martin, W.P.⁴

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