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Volumn 68, Issue 24, 2012, Pages 4541-4580

Enantioselective organocatalytic aldol reaction using small organic molecules

Author keywords

Enamine catalysis; Enol; Enolate; l Prolinamide; l Proline; Organocatalysis; Organocatalytic aldol; Primary amines; Self aldol; Thiourea; Unactivated ketones; Hydroxy phosphinate; Hydroxy phosphonate

Indexed keywords

ENAMINE; KETONE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; PROLINE; THIOUREA;

EID: 84861222515     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.03.099     Document Type: Review
Times cited : (166)

References (427)
  • 22
    • 84861221097 scopus 로고
    • German Patent DE 2102623
    • Hajos, Z. G.; Parrish, D. R., German Patent DE 2102623, 1971.
    • (1971)
    • Hajos, Z.G.1    Parrish, D.R.2
  • 34
    • 4143095871 scopus 로고    scopus 로고
    • Wiley-VCH GmbH KGaA Weinheim For a review, see; List, B. Acc. Chem. Res. 2004, 37, 548
    • B. List R. Mahrwald, Modern Aldol Reactions Vol. 1 2004 Wiley-VCH GmbH KGaA Weinheim 161 For a review, see; List, B. Acc. Chem. Res. 2004, 37, 548
    • (2004) Modern Aldol Reactions , vol.1 , pp. 161
    • List, B.1    Mahrwald, R.2
  • 45
    • 77954320410 scopus 로고    scopus 로고
    • For NMR investigations on l-proline-catalyzed aldol reactions, see
    • For NMR investigations on l-proline-catalyzed aldol reactions, see; M.B. Schmid, K. Zeitler, and R.M. Gschwind Angew. Chem., Int. Ed. 49 2010 4997
    • (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 4997
    • Schmid, M.B.1    Zeitler, K.2    Gschwind, R.M.3
  • 58
    • 3042809540 scopus 로고    scopus 로고
    • For a dynamic kinetic resolution of atropisomeric amides, see
    • For a dynamic kinetic resolution of atropisomeric amides, see; V. Chan, J.G. Kim, C. Jimeno, P.J. Carroll, and P.J. Walsh Org. Lett. 6 2004 2051
    • (2004) Org. Lett. , vol.6 , pp. 2051
    • Chan, V.1    Kim, J.G.2    Jimeno, C.3    Carroll, P.J.4    Walsh, P.J.5
  • 63
    • 3042616453 scopus 로고    scopus 로고
    • For l-prolinol catalyzed fluoroaldol reactions providing anti-α-fluoro-β-hydroxy ketones, see
    • For l-prolinol catalyzed fluoroaldol reactions providing anti-α-fluoro-β-hydroxy ketones, see; G. Zhong, J. Fan, and C.F. Barbas III Tetrahedron Lett. 45 2004 5681
    • (2004) Tetrahedron Lett. , vol.45 , pp. 5681
    • Zhong, G.1    Fan, J.2    Barbas Iii, C.F.3
  • 69
    • 33847163532 scopus 로고    scopus 로고
    • For a catalytic direct asymmetric aldolreactions of aldehydes with methylthioacetone and fluoroacetone, see
    • For a catalytic direct asymmetric aldolreactions of aldehydes with methylthioacetone and fluoroacetone, see: X.-Y. Xu, Y.-Z. Wang, L.-F. Cun, and L.-Z. Gong Tetrahedron: Asymmetry 18 2007 237
    • (2007) Tetrahedron: Asymmetry , vol.18 , pp. 237
    • Xu, X.-Y.1    Wang, Y.-Z.2    Cun, L.-F.3    Gong, L.-Z.4
  • 81
    • 70449345895 scopus 로고    scopus 로고
    • For a review of direct aldol reactions in aqueous medium, see
    • For a review of direct aldol reactions in aqueous medium, see; M. Raj, and V.K. Singh Chem. Commun. 2009 6687
    • (2009) Chem. Commun. , pp. 6687
    • Raj, M.1    Singh, V.K.2
  • 96
    • 28944440486 scopus 로고    scopus 로고
    • For organocatalytic l-proline catalyzed synthesis of (-)-(5R,6S)-6- acetoxyhexadecanolide, see
    • For organocatalytic l-proline catalyzed synthesis of (-)-(5R,6S)-6- acetoxyhexadecanolide, see; H. Ikishima, Y. Sekiguchi, Y. Ichikawa, and H. Kotsuki Tetrahedron 62 2006 311
    • (2006) Tetrahedron , vol.62 , pp. 311
    • Ikishima, H.1    Sekiguchi, Y.2    Ichikawa, Y.3    Kotsuki, H.4
  • 121
    • 4644319315 scopus 로고    scopus 로고
    • For a desymmetrization of 4-substituted ketones via an enantioselective enolborination, see
    • G.-J. ten Brink, I.W.C.E. Arends, and R.A. Sheldon Chem. Rev. 104 2004 4105 For a desymmetrization of 4-substituted ketones via an enantioselective enolborination, see
    • (2004) Chem. Rev. , vol.104 , pp. 4105
    • Ten Brink, G.-J.1    Arends, I.W.C.E.2    Sheldon, R.A.3
  • 129
    • 28944450978 scopus 로고    scopus 로고
    • For kinetic isotope effects and thermodynamic studies of nornicotine-catalyzed aqueous aldol reaction, see
    • For kinetic isotope effects and thermodynamic studies of nornicotine-catalyzed aqueous aldol reaction, see; C.J. Rogers, T.J. Dickerson, and K.D. Janda Tetrahedron 62 2006 352
    • (2006) Tetrahedron , vol.62 , pp. 352
    • Rogers, C.J.1    Dickerson, T.J.2    Janda, K.D.3
  • 131
    • 28944449583 scopus 로고    scopus 로고
    • For effect of additives on the proline catalyzed ketone-aldehyde aldol reactions, see
    • For effect of additives on the proline catalyzed ketone-aldehyde aldol reactions, see; P.M. Pihko, K.M. Laurikainen, A. Usano, A.I. Nyberg, and J.A. Kaavi Tetrahedron 62 2006 317
    • (2006) Tetrahedron , vol.62 , pp. 317
    • Pihko, P.M.1    Laurikainen, K.M.2    Usano, A.3    Nyberg, A.I.4    Kaavi, J.A.5
  • 137
    • 0028459111 scopus 로고
    • For a yeast-mediated asymmetric reduction of bicyclo[3.3.1]nonan-2,8- dione, see
    • For a yeast-mediated asymmetric reduction of bicyclo[3.3.1]nonan-2,8- dione, see; K. Mori, S. Takayama, and M. Kido Bioorg. Med. Chem. 2 1994 395
    • (1994) Bioorg. Med. Chem. , vol.2 , pp. 395
    • Mori, K.1    Takayama, S.2    Kido, M.3
  • 144
    • 0000776283 scopus 로고    scopus 로고
    • For direct aldol reactions catalyzed by poly(ethylene glycol)-supported proline, see
    • For direct aldol reactions catalyzed by poly(ethylene glycol)-supported proline, see; M. Benaglia, G. Celentano, and F. Cozzi Adv. Synth. Catal. 343 2001 171
    • (2001) Adv. Synth. Catal. , vol.343 , pp. 171
    • Benaglia, M.1    Celentano, G.2    Cozzi, F.3
  • 167
    • 20544474258 scopus 로고    scopus 로고
    • For synthesis of quaternary carbon containing β-hydroxy carbonyl compounds, see
    • For synthesis of quaternary carbon containing β-hydroxy carbonyl compounds, see; W. Wang, H. Li, and J. Wang Tetrahedron Lett. 46 2005 5077
    • (2005) Tetrahedron Lett. , vol.46 , pp. 5077
    • Wang, W.1    Li, H.2    Wang, J.3
  • 213
    • 33947605163 scopus 로고    scopus 로고
    • For Micheal addition of ketone to α,β-unsaturated nitro olefins, see
    • For Micheal addition of ketone to α,β-unsaturated nitro olefins, see; V. Maya, and V.K. Singh Org. Lett. 9 2009 1117
    • (2009) Org. Lett. , vol.9 , pp. 1117
    • Maya, V.1    Singh, V.K.2
  • 225
    • 23044482261 scopus 로고    scopus 로고
    • For a heterogeneous catalysis by solid-supported proline-terminated peptides, see
    • For a heterogeneous catalysis by solid-supported proline-terminated peptides, see; M.R.M. Andreae, and A.P. Davis Tetrahedron: Asymmetry 16 2005 2487
    • (2005) Tetrahedron: Asymmetry , vol.16 , pp. 2487
    • Andreae, M.R.M.1    Davis, A.P.2
  • 282
    • 0001612035 scopus 로고
    • E.J. Griffith, M. Grayson, John Wiley New York
    • D. Redmore E.J. Griffith, M. Grayson, Topics in Phosphorus Chemistry vol. 8 1976 John Wiley New York 515 585
    • (1976) Topics in Phosphorus Chemistry , vol.8 , pp. 515-585
    • Redmore, D.1
  • 286
    • 84861225140 scopus 로고    scopus 로고
    • U.S. Patent US 20100016258
    • Lynch, K. R.; MacDonald, T. L. U.S. Patent US 20100016258, 2010.
    • (2010)
    • Lynch, K.R.1    MacDonald, T.L.2
  • 330
    • 0031313763 scopus 로고    scopus 로고
    • For a review of aldolase enzymes in carbohydrate synthesis, see
    • For a review of aldolase enzymes in carbohydrate synthesis, see: S. Takayama, G.J. McGarvey, and C.-H. Wong Chem. Soc. Rev. 26 1997 407
    • (1997) Chem. Soc. Rev. , vol.26 , pp. 407
    • Takayama, S.1    McGarvey, G.J.2    Wong, C.-H.3
  • 360
    • 77952562733 scopus 로고    scopus 로고
    • For a supramolecular diamine catalyzed direct aldol reaction, see
    • For a supramolecular diamine catalyzed direct aldol reaction, see; S. Hu, J. Li, J. Xiang, J. Pan, S. Luo, and J.-P. Cheng J. Am. Chem. Soc. 132 2010 7216
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 7216
    • Hu, S.1    Li, J.2    Xiang, J.3    Pan, J.4    Luo, S.5    Cheng, J.-P.6
  • 410
    • 66249121705 scopus 로고    scopus 로고
    • references cited therein
    • N. Palyam, and M. Majewski J. Org. Chem. 74 2009 4390 and references cited therein
    • (2009) J. Org. Chem. , vol.74 , pp. 4390
    • Palyam, N.1    Majewski, M.2


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