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Volumn 46, Issue 44, 2007, Pages 8431-8435

Water-compatible iminium activation: Organocatalytic Michael reactions of carbon-centered nucleophiles with enals

Author keywords

Aldehydes; Amines; Asymmetric catalysis; Iminium activation; Organocatalysis

Indexed keywords

ALDEHYDES; AMINES; CATALYST ACTIVITY; CHEMICAL BONDS; CHIRALITY; ENANTIOSELECTIVITY;

EID: 36148957495     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200703261     Document Type: Article
Times cited : (222)

References (90)
  • 1
    • 36148960212 scopus 로고    scopus 로고
    • General reviews: a Organic Synthesis in Water (Ed.: P. A. Grieco), Blackie Academic & Profesional, London, 1998;
    • General reviews: a) Organic Synthesis in Water (Ed.: P. A. Grieco), Blackie Academic & Profesional, London, 1998;
  • 3
    • 24044470646 scopus 로고    scopus 로고
    • c) C.-J. Li, Chem. Rev. 2005, 105, 3095-3165;
    • (2005) Chem. Rev , vol.105 , pp. 3095-3165
    • Li, C.-J.1
  • 6
    • 34250726521 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 3798-3800.
    • (2007) Chem. Int. Ed , vol.46 , pp. 3798-3800
    • Angew1
  • 7
    • 0003476436 scopus 로고    scopus 로고
    • For successful metal catalysis in aqueous systems, see: a, Eds, B. Cornils, W. A. Herrman, Wiley-VCH, Weinheim
    • For successful metal catalysis in aqueous systems, see: a) Aqueous-Phase Organometallic Catalysis (Eds.: B. Cornils, W. A. Herrman), Wiley-VCH, Weinheim, 1998;
    • (1998) Aqueous-Phase Organometallic Catalysis
  • 11
    • 0001644556 scopus 로고    scopus 로고
    • Reviews on organocatalysis: a
    • Reviews on organocatalysis: a) P. I. Dalko, L. Moisan, Angew. Chem. 2001, 113, 3840-3864;
    • (2001) Angew. Chem , vol.113 , pp. 3840-3864
    • Dalko, P.I.1    Moisan, L.2
  • 12
    • 0035886887 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 3726-3748;
    • (2001) Chem. Int. Ed , vol.40 , pp. 3726-3748
    • Angew1
  • 15
    • 6044269452 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 5138-5175;
    • (2004) Chem. Int. Ed , vol.43 , pp. 5138-5175
    • Angew1
  • 18
    • 36148951844 scopus 로고    scopus 로고
    • See also special issues on organocatalysis: f Acc. Chem. Res. 2004, 37(8);
    • See also special issues on organocatalysis: f) Acc. Chem. Res. 2004, 37(8);
  • 19
    • 36148965253 scopus 로고    scopus 로고
    • 9-10
    • g) Adv. Synth. Cat. 2004, 346(9-10).
    • (2004) Adv. Synth. Cat , vol.346
  • 20
    • 0037012379 scopus 로고    scopus 로고
    • Aldol reactions: a T. J. Dickerson, K. D. Janda, J. Am. Chem. Soc. 2002, 124, 3220-3221;
    • Aldol reactions: a) T. J. Dickerson, K. D. Janda, J. Am. Chem. Soc. 2002, 124, 3220-3221;
  • 22
    • 2942641357 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 1983-1986;
    • (2004) Chem. Int. Ed , vol.43 , pp. 1983-1986
    • Angew1
  • 27
    • 33748655418 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 5527-5529;
    • (2006) Chem. Int. Ed , vol.45 , pp. 5527-5529
    • Angew1
  • 31
    • 33947545143 scopus 로고    scopus 로고
    • Mannich reaction: i L. Cheng, X. Wu, Y. Lu, Org. Biomol. Chem. 2007, 5, 1018-1020;
    • Mannich reaction: i) L. Cheng, X. Wu, Y. Lu, Org. Biomol. Chem. 2007, 5, 1018-1020;
  • 32
    • 33646142092 scopus 로고    scopus 로고
    • Michael reactions: j N. Mase, K. Watanabe, H. Yoda, K. Takabe, F. Tanaka, C. F. Barbas III, J. Am. Chem. Soc. 2006, 128, 4966-4967;
    • Michael reactions: j) N. Mase, K. Watanabe, H. Yoda, K. Takabe, F. Tanaka, C. F. Barbas III, J. Am. Chem. Soc. 2006, 128, 4966-4967;
  • 38
    • 0037043180 scopus 로고    scopus 로고
    • Reviews on enamine catalysis: a
    • Reviews on enamine catalysis: a) B. List, Tetrahedron 2002, 58, 5573-5590;
    • (2002) Tetrahedron , vol.58 , pp. 5573-5590
    • List, B.1
  • 43
    • 33845765822 scopus 로고    scopus 로고
    • For a recent exchange on the enamine-based organocatalysis carried out in systems containing water, see: a
    • For a recent exchange on the enamine-based organocatalysis carried out in systems containing water, see: a) A. P. Brogan, T. J. Dickerson, K. D. Janda, Angew. Chem. 2006, 118, 8278-8280;
    • (2006) Angew. Chem , vol.118 , pp. 8278-8280
    • Brogan, A.P.1    Dickerson, T.J.2    Janda, K.D.3
  • 44
    • 33845728625 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 8100-8102;
    • (2006) Chem. Int. Ed , vol.45 , pp. 8100-8102
    • Angew1
  • 45
    • 34250364382 scopus 로고    scopus 로고
    • b) Y. Hayashi, Angew. Chem. 2006, 118, 8281-8282;
    • (2006) Angew. Chem , vol.118 , pp. 8281-8282
    • Hayashi, Y.1
  • 46
    • 33845788846 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 8103-8104;
    • (2006) Chem. Int. Ed , vol.45 , pp. 8103-8104
    • Angew1
  • 47
    • 36148948717 scopus 로고    scopus 로고
    • see also Ref, 2
    • c) see also Ref. [2].
  • 48
    • 36148973270 scopus 로고    scopus 로고
    • For the uncovering of the iminium activation concept in asymmetric catalysis, see: a
    • For the uncovering of the iminium activation concept in asymmetric catalysis, see: a) K. A. Ahrendt, C. J. Borths, D. W. C. MacMilian, J. Am. Chem. Soc. 2000, 122, 9874-9875.
    • (2000) J. Am. Chem. Soc , vol.122 , pp. 9874-9875
    • Ahrendt, K.A.1    Borths, C.J.2    MacMilian, D.W.C.3
  • 50
    • 34250613134 scopus 로고    scopus 로고
    • For recent advances in asymmetric organocatalytic 1,4-additions, see: c
    • For recent advances in asymmetric organocatalytic 1,4-additions, see: c) S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701-1716;
    • (2007) Eur. J. Org. Chem , pp. 1701-1716
    • Tsogoeva, S.B.1
  • 53
    • 27844508553 scopus 로고    scopus 로고
    • Epoxidations: a W. Zhuang, M. Marigo, K. A. Jørgensen, Org. Biomol. Chem. 2005, 3, 3883-3885;
    • Epoxidations: a) W. Zhuang, M. Marigo, K. A. Jørgensen, Org. Biomol. Chem. 2005, 3, 3883-3885;
  • 55
    • 33751571805 scopus 로고    scopus 로고
    • Conjugate 1,4-additions of ketoesters: c A. Carlone, M. Marigo, C. North, A. Landa, K. A. Jørgensen, Chem. Commun. 2006, 4928-4930.
    • Conjugate 1,4-additions of ketoesters: c) A. Carlone, M. Marigo, C. North, A. Landa, K. A. Jørgensen, Chem. Commun. 2006, 4928-4930.
  • 56
    • 34248567850 scopus 로고    scopus 로고
    • Conjugate additions of thiols: d T. Ishino, T. Oriyama, Chem. Lett. 2007, 36, 550-551.
    • Conjugate additions of thiols: d) T. Ishino, T. Oriyama, Chem. Lett. 2007, 36, 550-551.
  • 57
    • 36148976914 scopus 로고    scopus 로고
    • For instance, while the conjugate addition of β-keto esters to enals catalyzed by a diarylprolinol silyl ether has been reported to occur in aqueous solutions (Ref. [9c]), the parent addition of malonates and malononitriles appears to work sluggishly if at all: a) S. Brandau, A. Landa, J. Franzén, M. Marigo, K. A. Jørgensen, Angew. Chem. 2006, 118, 4411-4415;
    • For instance, while the conjugate addition of β-keto esters to enals catalyzed by a diarylprolinol silyl ether has been reported to occur in aqueous solutions (Ref. [9c]), the parent addition of malonates and malononitriles appears to work sluggishly if at all: a) S. Brandau, A. Landa, J. Franzén, M. Marigo, K. A. Jørgensen, Angew. Chem. 2006, 118, 4411-4415;
  • 58
    • 33746290813 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 4305-4309;
    • (2006) Chem. Int. Ed , vol.45 , pp. 4305-4309
    • Angew1
  • 60
    • 34248192461 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 1101-1104.
    • (2007) Chem. Int. Ed , vol.46 , pp. 1101-1104
    • Angew1
  • 61
    • 36148972548 scopus 로고    scopus 로고
    • For details, see the Supporting Information
    • For details, see the Supporting Information.
  • 62
    • 36148987731 scopus 로고    scopus 로고
    • For pertinent information on this subject, see: a
    • For pertinent information on this subject, see: a) Ref. [8b];
    • , vol.8 b
    • Ref1
  • 64
    • 33845505476 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 7876-7880.
    • (2006) Chem. Int. Ed , vol.45 , pp. 7876-7880
    • Angew1
  • 66
    • 0346339657 scopus 로고    scopus 로고
    • For the chemistry and transformations of the nitro group, see: a
    • For the chemistry and transformations of the nitro group, see: a) R. Ballini, M. Petrini, Tetrahedron 2004, 60, 1017-1047;
    • (2004) Tetrahedron , vol.60 , pp. 1017-1047
    • Ballini, R.1    Petrini, M.2
  • 71
    • 0000497004 scopus 로고    scopus 로고
    • For conjugate additions to enones involving iminium activation, see: d
    • For conjugate additions to enones involving iminium activation, see: d) S. Hanessian, V. Pham, Org. Lett. 2000, 2, 2975-2978;
    • (2000) Org. Lett , vol.2 , pp. 2975-2978
    • Hanessian, S.1    Pham, V.2
  • 77
    • 36148936859 scopus 로고    scopus 로고
    • This hypothesis correlates well with the observed variation in enantioselectivity from the neat reaction to the aqueous reaction, as water may disrupt any well-organized hydrogen-bond network. For computational models supporting hydrogen bonding between the catalyst OH group and the substrate NO2 group in a related system, see: C. Palomo, S. Vera, A. Mielgo, E. Gómez-Bengoa, Angew. Chem. 2006, 118, 6130-6133;
    • 2 group in a related system, see: C. Palomo, S. Vera, A. Mielgo, E. Gómez-Bengoa, Angew. Chem. 2006, 118, 6130-6133;
  • 78
    • 33748791724 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 5984-5987.
    • (2006) Chem. Int. Ed , vol.45 , pp. 5984-5987
    • Angew1
  • 79
    • 36148935327 scopus 로고    scopus 로고
    • Transformation into the alcohols or ester derivatives was required to avoid partial decomposition of the aldehyde products during chromatographic isolation
    • Transformation into the alcohols or ester derivatives was required to avoid partial decomposition of the aldehyde products during chromatographic isolation.
  • 81
    • 6044253425 scopus 로고    scopus 로고
    • For amine-catalyzed intramolecular Michael reactions of aldehydes, see: a
    • For amine-catalyzed intramolecular Michael reactions of aldehydes, see: a) M. T. E. Fonseca, B. List, Angew. Chem. 2004, 116, 4048-4050;
    • (2004) Angew. Chem , vol.116 , pp. 4048-4050
    • Fonseca, M.T.E.1    List, B.2
  • 82
    • 4544361465 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 3958-3960;
    • (2004) Chem. Int. Ed , vol.43 , pp. 3958-3960
    • Angew1
  • 84
    • 25444470782 scopus 로고    scopus 로고
    • For intermolecular versions, see: (to enones) c
    • For intermolecular versions, see: (to enones) c) Y. Chi, S. H. Gellman, Org. Lett. 2005, 7, 4253-4256;
    • (2005) Org. Lett , vol.7 , pp. 4253-4256
    • Chi, Y.1    Gellman, S.H.2
  • 87
    • 26444568120 scopus 로고    scopus 로고
    • (to vinylsulfones) f) S. Mossé, A. Alexakis, Org. Lett. 2005, 7, 4361-4364;
    • (to vinylsulfones) f) S. Mossé, A. Alexakis, Org. Lett. 2005, 7, 4361-4364;
  • 88
    • 33846919087 scopus 로고    scopus 로고
    • (to maleimides) g) G.-L. Zhao, Y. Xu, H. Sundén, L. Eriksson, M. Sayah, A. Córdova, Chem. Commun. 2007, 734-735.
    • (to maleimides) g) G.-L. Zhao, Y. Xu, H. Sundén, L. Eriksson, M. Sayah, A. Córdova, Chem. Commun. 2007, 734-735.
  • 89
    • 33645929387 scopus 로고    scopus 로고
    • Amine-catalyzed Michael addition of ketones to chalcones: h J. Wang, H. Li, L. Zu, W. Wang, Adv. Synth. Catal. 2006, 348, 425-428.
    • Amine-catalyzed Michael addition of ketones to chalcones: h) J. Wang, H. Li, L. Zu, W. Wang, Adv. Synth. Catal. 2006, 348, 425-428.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.