메뉴 건너뛰기




Volumn 37, Issue 2, 2004, Pages 102-112

The Direct Catalytic Asymmetric Mannich Reaction

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID; AMINE; AMINO ACID; AMINOALCOHOL; BETA AMINO ACID; BETA LACTAM; IMINE; LACTAM; ORGANOMETALLIC COMPOUND;

EID: 1642415515     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar030231l     Document Type: Article
Times cited : (779)

References (88)
  • 4
    • 37049166036 scopus 로고
    • Synthesis of Tropinone
    • The first example of the application of the Mannich reaction to natural product synthesis is attributed to Robinson in his synthesis of tropinone: Robinson, R. Synthesis of Tropinone. J. Chem. Soc. 1917, 762-768.
    • (1917) J. Chem. Soc. , pp. 762-768
    • Robinson, R.1
  • 5
    • 0000733768 scopus 로고
    • Trost, B. M., Flemming, I., Eds.; Pergamon Press: New York, Chapter 4.1
    • For excellent reviews, see: (a) Kleinmann, E. F. In Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 4.1.
    • (1991) Comprehensive Organic Synthesis , vol.2
    • Kleinmann, E.F.1
  • 7
    • 0000862669 scopus 로고    scopus 로고
    • Catalytic Enantioselective Addition to Imines
    • (c) Kobayashi, S.; Ishitani, H. Catalytic Enantioselective Addition to Imines. Chem. Rev. 1999, 99, 1069-1094.
    • (1999) Chem. Rev. , vol.99 , pp. 1069-1094
    • Kobayashi, S.1    Ishitani, H.2
  • 8
    • 0002927738 scopus 로고    scopus 로고
    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer; Berlin
    • (d) Denmark, S.; Nicaise, O. J.-C. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer; Berlin, 1999; Vol. 2, p 93.
    • (1999) Comprehensive Asymmetric Catalysis , vol.2 , pp. 93
    • Denmark, S.1    Nicaise, O.J.-C.2
  • 10
    • 0002478426 scopus 로고    scopus 로고
    • Preparation and Use of a New Chiral Glycine Derivative, (R)- and (S)-tert-Butyl 2-tert-butyl-4-methoxy-2,5-dihydroimidazole-1-carboxylate (BDI), in Amino Acid Synthesis
    • (a) Seebach, D.; Hoffmann, M. Preparation and Use of a New Chiral Glycine Derivative, (R)- and (S)-tert-Butyl 2-tert-butyl-4-methoxy-2,5-dihydroimidazole-1-carboxylate (BDI), in Amino Acid Synthesis. Eur. J. Org. Chem. 1998, 1337-1351.
    • (1998) Eur. J. Org. Chem. , pp. 1337-1351
    • Seebach, D.1    Hoffmann, M.2
  • 11
    • 0034836271 scopus 로고    scopus 로고
    • Stereocontrolled Asymmetric Synthesis of α-Hydroxy-β-Amino Acids, a Stereodivergent Approach
    • and references therein
    • (b) Aoyagi, Y.; Jain, R. P.; Williams, R. M. Stereocontrolled Asymmetric Synthesis of α-Hydroxy-β-Amino Acids, a Stereodivergent Approach. J. Am. Chem. Soc. 2001, 123, 3472-3477 and references therein.
    • (2001) J. Am. Chem. Soc , vol.123 , pp. 3472-3477
    • Aoyagi, Y.1    Jain, R.P.2    Williams, R.M.3
  • 12
    • 4243927866 scopus 로고
    • Boschke, F. L., Ed.; Springer-Verlag: Berlin
    • (c) Schöllkopf, U. In Topics in Current Chemistry; Boschke, F. L., Ed.; Springer-Verlag: Berlin, 1983; Vol. 109, pp 45-85.
    • (1983) Topics in Current Chemistry , vol.109 , pp. 45-85
    • Schöllkopf, U.1
  • 13
    • 33748468588 scopus 로고
    • New Procedure for the Direct Generation of Titanium Enolates. Diastereoselective Bond Construction with Representative Electrophiles
    • (d) Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. New Procedure for the Direct Generation of Titanium Enolates. Diastereoselective Bond Construction with Representative Electrophiles. J. Am. Chem. Soc. 1990, 112, 8215-8216.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 8215-8216
    • Evans, D.A.1    Urpi, F.2    Somers, T.C.3    Clark, J.S.4    Bilodeau, M.T.5
  • 14
    • 0000698759 scopus 로고
    • Synthesis of Diastereo- and Enantiomerically Pure α-Amino-γ -Acid Esters by Reaction of Acyl Imino-Acetates with Enamines Derived from 6-Membered Ketones
    • (e) Kober, R.; Papadopoulos, K.; Miltz, W.; Enders, D.; Steglich, W.; Reuter, H.; Puff, H. Synthesis of Diastereo- and Enantiomerically Pure α-Amino-γ-Acid Esters by Reaction of Acyl Imino-Acetates with Enamines Derived from 6-Membered Ketones. Tetrahedron 1985, 42, 1693-1701.
    • (1985) Tetrahedron , vol.42 , pp. 1693-1701
    • Kober, R.1    Papadopoulos, K.2    Miltz, W.3    Enders, D.4    Steglich, W.5    Reuter, H.6    Puff, H.7
  • 15
    • 0037167030 scopus 로고    scopus 로고
    • Design and Synthesis of a Novel Class of Sugar-Peptide Hybrids: C-linked Glyco-β-Amino Acids through a Stereoselective "Acetate" Mannich Reaction as the Key Element
    • and references therein
    • (f) Palomo, C.; Oiarbide, M.; Landa, A.; Gonzales-Rego, M. C.; Garcia, J. M.; Gonzales, A.; Odriozola, J. M.; Martin-Pastor, M.; Linden, A. Design and Synthesis of a Novel Class of Sugar-Peptide Hybrids: C-linked Glyco-β-Amino Acids through a Stereoselective "Acetate" Mannich Reaction as the Key Element. J. Am. Chem. Soc. 2002, 124, 8637-8643 and references therein.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 8637-8643
    • Palomo, C.1    Oiarbide, M.2    Landa, A.3    Gonzales-Rego, M.C.4    Garcia, J.M.5    Gonzales, A.6    Odriozola, J.M.7    Martin-Pastor, M.8    Linden, A.9
  • 16
    • 0030788354 scopus 로고    scopus 로고
    • Catalytic Enantioselective Mannich-type Reactions using a Novel Chiral Zirconium Catalyst
    • (a) Ishitani, H.; Ueno, M.; Kobayashi, S. Catalytic Enantioselective Mannich-type Reactions using a Novel Chiral Zirconium Catalyst. J. Am. Chem. Soc. 1997, 119, 7153-7154.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 7153-7154
    • Ishitani, H.1    Ueno, M.2    Kobayashi, S.3
  • 17
    • 0037157202 scopus 로고    scopus 로고
    • The Catalytic Asymmetric Mannich-type Reaction in Aqueous Media
    • (b) Kobayashi, S.; Hamada, T.; Manabe, K. The Catalytic Asymmetric Mannich-type Reaction in Aqueous Media. J. Am. Chem. Soc. 2002, 124, 5640-5641.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 5640-5641
    • Kobayashi, S.1    Hamada, T.2    Manabe, K.3
  • 18
    • 0034734313 scopus 로고    scopus 로고
    • Enantioselective Mannich-type Reactions using a Novel chiral Zirconium Catalyst for the Synthesis of Optically β-Amino Acid Derivatives
    • (c) Ishitani, H.; Ueno, S.; Kobayashi, S. Enantioselective Mannich-type Reactions using a Novel chiral Zirconium Catalyst for the Synthesis of Optically β-Amino Acid Derivatives. J. Am. Chem. Soc. 2000, 122, 8180-8186.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 8180-8186
    • Ishitani, H.1    Ueno, S.2    Kobayashi, S.3
  • 19
    • 0032542749 scopus 로고    scopus 로고
    • Enantioselective Addition of Enol Silyl Ethers to Imines Catalyzed by Palladium Complexes: A Novel Way to Optically Active Acylalanine Derivatives
    • (a) Hagiwara, E.; Fujii, A.; Sodeoka, M. Enantioselective Addition of Enol Silyl Ethers to Imines Catalyzed by Palladium Complexes: A Novel Way to Optically Active Acylalanine Derivatives. J. Am Chem. Soc. 1998, 120, 2474-2475.
    • (1998) J. Am Chem. Soc. , vol.120 , pp. 2474-2475
    • Hagiwara, E.1    Fujii, A.2    Sodeoka, M.3
  • 20
    • 0033575073 scopus 로고    scopus 로고
    • Mechanism of Palladium Complex-Catalyzed Enantioselective Mannich-Type Reaction: Characterization of A Novel Binuclear Palladium Enolate Complex
    • (b) Fujii, A.; Hagiwara, E.; Sodeoka, M. Mechanism of Palladium Complex-Catalyzed Enantioselective Mannich-Type Reaction: Characterization of A Novel Binuclear Palladium Enolate Complex. J. Am Chem. Soc. 1999, 121, 545-556.
    • (1999) J. Am Chem. Soc. , vol.121 , pp. 545-556
    • Fujii, A.1    Hagiwara, E.2    Sodeoka, M.3
  • 21
    • 0001209391 scopus 로고    scopus 로고
    • A Novel Synthesis of α-Amino Acid Derivatives through Catalytic Enantioselective Ene-Reactions of α-Imino Esters
    • (a) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. A Novel Synthesis of α-Amino Acid Derivatives through Catalytic, Enantioselective Ene-Reactions of α-Imino Esters. J. Am. Chem. Soc. 1998, 120, 4548-4549.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 4548-4549
    • Ferraris, D.1    Young, B.2    Dudding, T.3    Lectka, T.4
  • 22
    • 0037045227 scopus 로고    scopus 로고
    • Catalytic, Enantioselective Alkylation of α-Imino Esters: The Synthesis of Nonnatural α-Amino Acid Derivatives
    • and references therein
    • (b) Ferraris D.; Young, B.; Cox, C.; Dudding, T.; Drury, W. J., III; Ryzhkov, L.; Taggi, T.; Lectka, T. Catalytic, Enantioselective Alkylation of α-Imino Esters: The Synthesis of Nonnatural α-Amino Acid Derivatives. J. Am Chem. Soc. 2002, 124, 67-77 and references therein.
    • (2002) J. Am Chem. Soc. , vol.124 , pp. 67-77
    • Ferraris, D.1    Young, B.2    Cox, C.3    Dudding, T.4    Drury III, W.J.5    Ryzhkov, L.6    Taggi, T.7    Lectka, T.8
  • 23
    • 0037032312 scopus 로고    scopus 로고
    • Asymmetric Catalytic Mannich Reactions Catalyzed by Urea Derivatives: Enantioselective Synthesis of β-Aryl-β-Amino Acids
    • Wenzel, A. G.; Jacobsen, E. N. Asymmetric Catalytic Mannich Reactions Catalyzed by Urea Derivatives: Enantioselective Synthesis of β-Aryl-β-Amino Acids. J. Am Chem. Soc. 2002, 124, 12964-12965.
    • (2002) J. Am Chem. Soc. , vol.124 , pp. 12964-12965
    • Wenzel, A.G.1    Jacobsen, E.N.2
  • 24
    • 0026418434 scopus 로고
    • The Atom Economy: A Search for Synthetic Efficiency
    • Trost, B. M. The Atom Economy: A Search for Synthetic Efficiency. Science 1991, 254, 1471-1477.
    • (1991) Science , vol.254 , pp. 1471-1477
    • Trost, B.M.1
  • 25
    • 0037419152 scopus 로고    scopus 로고
    • Catalytic Asymmetric Mannich Reactions of Glycine Derivatives with Imines. A New Approach to Optically Active α,β-Diamino Acid Derivatives
    • For a new catalytic asymmetric Mannich-type reaction, see: Bernardi, L.; Gothelf, A. S.; Hazell, R. G.; Jørgensen, K. A. Catalytic Asymmetric Mannich Reactions of Glycine Derivatives with Imines. A New Approach to Optically Active α,β-Diamino Acid Derivatives. J. Org. Chem. 2003, 69, 2583-2591.
    • (2003) J. Org. Chem. , vol.69 , pp. 2583-2591
    • Bernardi, L.1    Gothelf, A.S.2    Hazell, R.G.3    Jørgensen, K.A.4
  • 26
    • 0030863510 scopus 로고    scopus 로고
    • Direct Catalytic Asymmetric Aldol reactions of Aldehydes with Unmodified Ketones
    • and references therein
    • See: Shibasaki, M.; Sasai, H.; Arai, T. Direct Catalytic Asymmetric Aldol reactions of Aldehydes with Unmodified Ketones. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871-1873 and references therein.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 1871-1873
    • Shibasaki, M.1    Sasai, H.2    Arai, T.3
  • 28
    • 0034801857 scopus 로고    scopus 로고
    • Direct Catalytic Asymmetric Aldol Reaction: Synthesis of Either syn- or anti-α,β-Dihydroxy Ketones
    • (b) Yoshikawa, N.; Kumagai, N.; Matsunaga, S.; Moll, G.; Ohshima, T.; Suzuki, T.; Shibasaki, M. Direct Catalytic Asymmetric Aldol Reaction: Synthesis of Either syn- or anti-α,β-Dihydroxy Ketones. J. Am. Chem. Soc. 2001, 123, 2466-2467.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 2466-2467
    • Yoshikawa, N.1    Kumagai, N.2    Matsunaga, S.3    Moll, G.4    Ohshima, T.5    Suzuki, T.6    Shibasaki, M.7
  • 29
    • 0034598534 scopus 로고    scopus 로고
    • Enantioselective Total Synthesis of Epothilone A using Multifunctional Asymmetric Catalyses
    • (c) Sawada, D.; Shibasaki, M. Enantioselective Total Synthesis of Epothilone A using Multifunctional Asymmetric Catalyses. Angew. Chem., Int. Ed. 2000, 39, 209-213.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 209-213
    • Sawada, D.1    Shibasaki, M.2
  • 31
    • 0037462104 scopus 로고    scopus 로고
    • Anti-Selective Direct Catalytic Asymmetric Mannich-type Reaction of Hydroxyketone Providing β-Amino Alcohols
    • Matsunaga, S.; Kumagai, N.; Harada, N.; Harada, S.; Shibasaki, M. anti-Selective Direct Catalytic Asymmetric Mannich-type Reaction of Hydroxyketone Providing β-Amino Alcohols. J. Am. Chem. Soc. 2003, 125, 4712-4713.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 4712-4713
    • Matsunaga, S.1    Kumagai, N.2    Harada, N.3    Harada, S.4    Shibasaki, M.5
  • 32
    • 0001392528 scopus 로고    scopus 로고
    • Stable, Storable, and Reusable Asymmetric Catalyst: A Novel La-linked-BINOL Complex for the Catalytic Asymmetric Michael Reaction
    • (a) Matsunaga, S.; Das, J.; Roels, J.; Vogel, E. M.; Yamomoto, N.; Iida, T. Yamaguchi, K.; Shibasaki, M. Stable, Storable, and Reusable Asymmetric Catalyst: A Novel La-linked-BINOL Complex for the Catalytic Asymmetric Michael Reaction. J. Am. Chem. Soc. 2000, 122, 6506-6507.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 6506-6507
    • Matsunaga, S.1    Das, J.2    Roels, J.3    Vogel, E.M.4    Yamomoto, N.5    Iida, T.6    Yamaguchi, K.7    Shibasaki, M.8
  • 35
    • 0034614028 scopus 로고    scopus 로고
    • A Direct Catalytic Enantioselective Aldol Reaction via a Novel Catalyst Design
    • (a) Trost, B. M.; Ito, H. A Direct Catalytic Enantioselective Aldol Reaction via a Novel Catalyst Design. J. Am. Chem. Soc. 2000, 122, 12003-12004.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 12003-12004
    • Trost, B.M.1    Ito, H.2
  • 36
    • 0034823456 scopus 로고    scopus 로고
    • Asymmetric Aldol Reaction via a Dinuclear Zinc Catalyst: α-Hydroxy Ketones as Donors
    • (b) Trost, B. M.; Ito, H.; Silcoff, E. Asymmetric Aldol Reaction via a Dinuclear Zinc Catalyst: α-Hydroxy Ketones as Donors. J. Am. Chem. Soc. 2001, 123, 3367-3368.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 3367-3368
    • Trost, B.M.1    Ito, H.2    Silcoff, E.3
  • 37
    • 0035833675 scopus 로고    scopus 로고
    • Direct Asymmetric Aldol Reactions of Acetone using Bimetallic Zinc Catalysts
    • (c) Trost, B. M.; Silcoff, E.; Ito, H. Direct Asymmetric Aldol Reactions of Acetone using Bimetallic Zinc Catalysts. Org. Lett. 2001, 3, 2497-2500.
    • (2001) Org. Lett. , vol.3 , pp. 2497-2500
    • Trost, B.M.1    Silcoff, E.2    Ito, H.3
  • 38
    • 0037438599 scopus 로고    scopus 로고
    • A Direct Catalytic Asymmetric Mannich-type Reaction to syn-Amino Alcohols
    • Trost, B. M.; Terrell, L. M. A Direct Catalytic Asymmetric Mannich-type Reaction to syn-Amino Alcohols. J. Am. Chem. Soc. 2003, 125, 338-339.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 338-339
    • Trost, B.M.1    Terrell, L.M.2
  • 39
    • 0036462501 scopus 로고    scopus 로고
    • "Second-Cycle"-Ligands: The Next Generation for Amino- and Dihydroxylation
    • and references therein
    • (a) Andersson, M. A.; Epple, R.; Fokin, V. V.; Sharpless, K. B. "Second-Cycle"-Ligands: The Next Generation for Amino- and Dihydroxylation. Angew. Chem., Int. Ed. 2002, 41, 472-475 and references therein.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 472-475
    • Andersson, M.A.1    Epple, R.2    Fokin, V.V.3    Sharpless, K.B.4
  • 40
    • 33748233248 scopus 로고    scopus 로고
    • Catalytic Asymmetric Aminohydroxylation (AA) of Olefins
    • (b) Li, G.; Chang, H.-T.; Sharpless, K. B. Catalytic Asymmetric Aminohydroxylation (AA) of Olefins. Angew. Chem., Int. Ed. Engl. 1996, 35, 451-454.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 451-454
    • Li, G.1    Chang, H.-T.2    Sharpless, K.B.3
  • 41
    • 0034700224 scopus 로고    scopus 로고
    • Catalytic Asymmetric Homo-Aldol Reaction of Pyruvate-a Chiral Lewis Acid Catalyst that Mimics Aldolase Enzymes
    • (a) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Catalytic Asymmetric Homo-Aldol Reaction of Pyruvate-a Chiral Lewis Acid Catalyst that Mimics Aldolase Enzymes. Chem. Commun. 2000, 2211-2212.
    • (2000) Chem. Commun. , pp. 2211-2212
    • Juhl, K.1    Gathergood, N.2    Jørgensen, K.A.3
  • 42
    • 0037139602 scopus 로고    scopus 로고
    • Catalytic Asymmetric Direct α-Amination Reactions of 2-Keto Esters: A Simple Synthetic Approach to Optically Active syn-β-Amino-α -hydroxy Esters
    • (b) Juhl, K.; Jørgensen, K. A. Catalytic Asymmetric Direct α-Amination Reactions of 2-Keto Esters: A Simple Synthetic Approach to Optically Active syn-β-Amino-α-hydroxy Esters. J. Am. Chem. Soc. 2002, 124, 2420-2421.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 2420-2421
    • Juhl, K.1    Jørgensen, K.A.2
  • 43
    • 0035902842 scopus 로고    scopus 로고
    • Catalytic Asymmetric Direct Mannich Reactions of Carbonyl Compounds with α-Imino Esters
    • Juhl, K.; Gathergood, N.; Jørgensen, K. A. Catalytic Asymmetric Direct Mannich Reactions of Carbonyl Compounds with α-Imino Esters. Angew. Chem., Int. Ed. 2001, 40, 2995-2997.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 2995-2997
    • Juhl, K.1    Gathergood, N.2    Jørgensen, K.A.3
  • 44
    • 0033936085 scopus 로고    scopus 로고
    • Chiral Bis(oxazoline) Copper(II) Complexes: Versatile Catalysts for Enantioselective Cycloaddition, Aldol, Michael, and Carbonyl Ene Reactions
    • 2-bisoxazoline-Lewis acid complexes, see: (a) Johnson, J. S.; Evans, D. A. Chiral Bis(oxazoline) Copper(II) Complexes: Versatile Catalysts for Enantioselective Cycloaddition, Aldol, Michael, and Carbonyl Ene Reactions. Acc. Chem. Res. 2000, 33, 325-335.
    • (2000) Acc. Chem. Res. , vol.33 , pp. 325-335
    • Johnson, J.S.1    Evans, D.A.2
  • 45
    • 0032772355 scopus 로고    scopus 로고
    • Catalytic Asymmetric Addition Reactions of Carbonyls. A Common Catalytic Approach
    • (b) Jørgensen, K. A.; Johannsen, M.; Yao, S.; Audrain, H.; Thorhauge, J. Catalytic Asymmetric Addition Reactions of Carbonyls. A Common Catalytic Approach. Acc. Chem. Res. 1999, 32, 605-613.
    • (1999) Acc. Chem. Res. , vol.32 , pp. 605-613
    • Jørgensen, K.A.1    Johannsen, M.2    Yao, S.3    Audrain, H.4    Thorhauge, J.5
  • 46
    • 0037495950 scopus 로고    scopus 로고
    • Direct Catalytic Asymmetric Mannich Reactions of Malonates and β-Keto Esters
    • Marigo, M.; Kjaersgaard, A.; Juhl, K.; Gathergood, N.; Jørgensen, K. A. Direct Catalytic Asymmetric Mannich Reactions of Malonates and β-Keto Esters. Chem.-Eur. J. 2003, 9, 2359-2367.
    • (2003) Chem.-Eur. J. , vol.9 , pp. 2359-2367
    • Marigo, M.1    Kjaersgaard, A.2    Juhl, K.3    Gathergood, N.4    Jørgensen, K.A.5
  • 47
    • 0032473509 scopus 로고    scopus 로고
    • The Catalytic Enantioselective Construction of Molecules with Quaternary Carbon Stereocenters
    • (a) Corey, E. J.; Guzman-Perez, A. The Catalytic Enantioselective Construction of Molecules with Quaternary Carbon Stereocenters. Angew. Chem., Int. Ed. 1998, 37, 388-401.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 388-401
    • Corey, E.J.1    Guzman-Perez, A.2
  • 48
    • 0035905575 scopus 로고    scopus 로고
    • Enantioselective Construction of Quaternary Stereocenters
    • (b) Christoffers, J.; Mann, A. Enantioselective Construction of Quaternary Stereocenters. Angew. Chem., Int. Ed. 2001, 40, 4591-4597.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 4591-4597
    • Christoffers, J.1    Mann, A.2
  • 49
    • 0035886887 scopus 로고    scopus 로고
    • Enantioselective Organocatalysis
    • (a) Dalko, P. I.; Moisan, L. Enantioselective Organocatalysis. Angew. Chem., Int. Ed. 2001, 40, 3726-3748.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 3726-3748
    • Dalko, P.I.1    Moisan, L.2
  • 50
    • 0037043180 scopus 로고    scopus 로고
    • Proline-Catalyzed Asymmetric Reactions
    • (b) List, B. Proline-Catalyzed Asymmetric Reactions. Tetrahedron 2002, 58, 5573-5590.
    • (2002) Tetrahedron , vol.58 , pp. 5573-5590
    • List, B.1
  • 51
    • 0035793248 scopus 로고    scopus 로고
    • The Application of L-Proline as an Enzyme Mimic and Further New Asymmetric Synthesis using Small Organic Molecules as Chiral Catalysts
    • (c) Gröger, J.; Wilken, J. The Application of L-Proline as an Enzyme Mimic and Further New Asymmetric Synthesis using Small Organic Molecules as Chiral Catalysts. Angew. Chem., Int. Ed. 2001, 40, 529-532.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 529-532
    • Gröger, J.1    Wilken, J.2
  • 52
    • 0037170944 scopus 로고    scopus 로고
    • Amino Acids and Peptides as Asymmetric Organocatalysts
    • (d) Jarvo, E. R.; Miller, S. J. Amino Acids and Peptides as Asymmetric Organocatalysts. Tetrahedron 2002, 58, 2481-2495.
    • (2002) Tetrahedron , vol.58 , pp. 2481-2495
    • Jarvo, E.R.1    Miller, S.J.2
  • 53
    • 0037416272 scopus 로고    scopus 로고
    • Proline-Catalyzed Asymmetric α-Amination of Aldehydes and Ketones-An Astonishingly Simple Access to Optically Active α-Hydrazino Carbonyl Compounds
    • (e) Duthaler, R. O. Proline-Catalyzed Asymmetric α-Amination of Aldehydes and Ketones-An Astonishingly Simple Access to Optically Active α-Hydrazino Carbonyl Compounds. Angew. Chem., Int. Ed. 2003, 42, 975-978.
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 975-978
    • Duthaler, R.O.1
  • 54
    • 1242334359 scopus 로고    scopus 로고
    • Asymmetric Synthesis of Optically Active Polycyclic Organic Compounds. German Patent DE 2102623, Jul 29, 1971
    • (a) Hajos, Z. G.; Parrish, D. R. Asymmetric Synthesis of Optically Active Polycyclic Organic Compounds. German Patent DE 2102623, Jul 29, 1971.
    • Hajos, Z.G.1    Parrish, D.R.2
  • 55
    • 33847804003 scopus 로고
    • Asymmetric Synthesis of Bicyclic Intermediates of Natural Product Chemistry
    • (b) Hajos, Z. G.; Parrish, D. R. Asymmetric Synthesis of Bicyclic Intermediates of Natural Product Chemistry. J. Org. Chem. 1974, 39, 1615-1621.
    • (1974) J. Org. Chem. , vol.39 , pp. 1615-1621
    • Hajos, Z.G.1    Parrish, D.R.2
  • 56
    • 1242266792 scopus 로고    scopus 로고
    • Optically Active 1,5-Indanone and 1,6-Naphthalenedionene. German Patent DE 2014757, Oct 7, 1971
    • (c) Eder, U.; Sauer, G.; Wiechert, R. Optically Active 1,5-Indanone and 1,6-Naphthalenedionene. German Patent DE 2014757, Oct 7, 1971.
    • Eder, U.1    Sauer, G.2    Wiechert, R.3
  • 57
    • 84981886574 scopus 로고
    • Total synthesis of optically active steroids. 6. New Type of Asymmetric Cyclization to Optically Active Steroid CD Partial Structures
    • (d) Eder, U.; Sauer, G.; Wiechert, R. Total synthesis of optically active steroids. 6. New Type of Asymmetric Cyclization to Optically Active Steroid CD Partial Structures. Angew. Chem., Int. Ed. Engl. 1971, 10, 496-497.
    • (1971) Angew. Chem., Int. Ed. Engl. , vol.10 , pp. 496-497
    • Eder, U.1    Sauer, G.2    Wiechert, R.3
  • 58
    • 0000246845 scopus 로고
    • Mechanism of the Proline-Catalyzed Enantioselective Aldol Reaction. Recent advances
    • (e) Agami, C. Mechanism of the Proline-Catalyzed Enantioselective Aldol Reaction. Recent advances. Bull. Soc. Chim. Fr. 1988, 499-507.
    • (1988) Bull. Soc. Chim. Fr. , pp. 499-507
    • Agami, C.1
  • 59
    • 11044223276 scopus 로고    scopus 로고
    • Total Synthesis of Taxol and Analogs
    • For example, for the total synthesis of Taxol, see: Danishefsky, S. J.; et al. Total Synthesis of Taxol and Analogs. J. Am. Chem. Soc. 1996, 118, 2843-2859.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 2843-2859
    • Danishefsky, S.J.1
  • 60
    • 0034721440 scopus 로고    scopus 로고
    • The Direct Catalytic Asymmetric Three-Component Mannich Reaction
    • (a) List B. The Direct Catalytic Asymmetric Three-Component Mannich Reaction. J. Am. Chem. Soc. 2000, 122, 9336-9337.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 9336-9337
    • List, B.1
  • 61
    • 0037028550 scopus 로고    scopus 로고
    • The Proline-Catalyzed Direct Asymmetric Three-Component Mannich Reaction: Scope, Optimization, and Application to the Highly Enantioselective Synthesis of 1,2-Amino Alcohols
    • (b) List B.; Porjalev, P.; Biller, W. T.; Martin, H. J. The Proline-Catalyzed Direct Asymmetric Three-Component Mannich Reaction: Scope, Optimization, and Application to the Highly Enantioselective Synthesis of 1,2-Amino Alcohols. J. Am. Chem. Soc. 2002, 124, 827-833.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 827-833
    • List, B.1    Porjalev, P.2    Biller, W.T.3    Martin, H.J.4
  • 62
    • 0034654216 scopus 로고    scopus 로고
    • Proline-Catalyzed Direct Asymmetric Aldol Reactions
    • (a) List, B.; Lerner, R. A.; Barbas, C. F., III. Proline-Catalyzed Direct Asymmetric Aldol Reactions. J. Am. Chem. Soc. 2000, 122, 2395-2396.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 2395-2396
    • List, B.1    Lerner, R.A.2    Barbas III, C.F.3
  • 63
    • 0034596299 scopus 로고    scopus 로고
    • Catalytic Asymmetric Synthesis of anti-1,2-Diols
    • (b) Notz, W.; List, B. Catalytic Asymmetric Synthesis of anti-1,2-Diols. J. Am. Chem. Soc. 2000, 122, 7386-7387.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 7386-7387
    • Notz, W.1    List, B.2
  • 64
    • 0001549125 scopus 로고    scopus 로고
    • Mannich-Type Reactions of Aldehydes, Amines, and Ketones in a Colloidal Dispersion System Created by a Brønsted Acid-Surfactant-Combined Catalyst in Water
    • and references therein
    • Manabe, K.; Kobayashi, S. Mannich-Type Reactions of Aldehydes, Amines, and Ketones in a Colloidal Dispersion System Created by a Brønsted Acid-Surfactant-Combined Catalyst in Water. Org. Lett. 1999, 1, 1965-1967 and references therein.
    • (1999) Org. Lett. , vol.1 , pp. 1965-1967
    • Manabe, K.1    Kobayashi, S.2
  • 66
    • 0034812506 scopus 로고    scopus 로고
    • Amino Acid-Catalyzed Direct Asymmetric Aldol Reactions: A Bioorganic Approach to Catalytic Asymmetric Carbon-Carbon Bond-Forming Reactions
    • Saktihvel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. Amino Acid-Catalyzed Direct Asymmetric Aldol Reactions: A Bioorganic Approach to Catalytic Asymmetric Carbon-Carbon Bond-Forming Reactions. J. Am. Chem. Soc. 2001, 123, 5260-5267.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 5260-5267
    • Saktihvel, K.1    Notz, W.2    Bui, T.3    Barbas III, C.F.4
  • 67
    • 0034596452 scopus 로고    scopus 로고
    • A Proline-Catalyzed Asymmetric Robinson Annulation Reaction
    • Bui, T.; Barbas, C. F., III. A Proline-Catalyzed Asymmetric Robinson Annulation Reaction. Tetrahedron Lett. 2000, 41, 6951-6954.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 6951-6954
    • Bui, T.1    Barbas III, C.F.2
  • 68
    • 0037244819 scopus 로고    scopus 로고
    • α-Imino Esters: Versatile Substrates for the Catalytic, Asymmetric Synthesis of α- and β-Amino Acids and β-Lactams
    • (a) Taggi, A. E.; Hafez, A. M.; Lectka, T. α-Imino Esters: Versatile Substrates for the Catalytic, Asymmetric Synthesis of α- and β-Amino Acids and β-Lactams. Acc. Chem. Res. 2002, 36, 10-19.
    • (2002) Acc. Chem. Res. , vol.36 , pp. 10-19
    • Taggi, A.E.1    Hafez, A.M.2    Lectka, T.3
  • 69
    • 0032484179 scopus 로고    scopus 로고
    • Catalytic Enantioselective Aza Diels-Alder Reactions of Imino Dienophiles
    • (b) Yao, S.; Johannsen, M.; Hazell, R. G.; Jørgensen, K. A. Catalytic Enantioselective Aza Diels-Alder Reactions of Imino Dienophiles. Angew. Chem., Int. Ed. 1998, 37, 3121-3124.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 3121-3124
    • Yao, S.1    Johannsen, M.2    Hazell, R.G.3    Jørgensen, K.A.4
  • 70
    • 0037028924 scopus 로고    scopus 로고
    • A Highly Enantioselective Amino Acid-Catalyzed Route to Functionalized α-Amino Acids
    • Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. A Highly Enantioselective Amino Acid-Catalyzed Route to Functionalized α-Amino Acids. J. Am. Chem. Soc. 2002, 124, 1844-1845.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 1844-1845
    • Córdova, A.1    Notz, W.2    Zhong, G.3    Betancort, J.M.4    Barbas III, C.F.5
  • 71
    • 0037059471 scopus 로고    scopus 로고
    • Proline-Catalyzed One-Step Asymmetric Synthesis of 5-Hydroxy-(2E) -hexenal from Acetaldehyde
    • Córdova, A.; Notz, W.; Barbas, C. F., III. Proline-Catalyzed One-Step Asymmetric Synthesis of 5-Hydroxy-(2E)-hexenal from Acetaldehyde. J. Org. Chem. 2002, 67, 301-303.
    • (2002) J. Org. Chem. , vol.67 , pp. 301-303
    • Córdova, A.1    Notz, W.2    Barbas III, C.F.3
  • 72
    • 0002462320 scopus 로고    scopus 로고
    • Direct Catalytic Asymmetric Aldol Reactions of Aldehydes
    • See also later important reports: (a) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Direct Catalytic Asymmetric Aldol Reactions of Aldehydes. Chem. Commun. 2002, 620-621.
    • (2002) Chem. Commun. , pp. 620-621
    • Bøgevig, A.1    Kumaragurubaran, N.2    Jørgensen, K.A.3
  • 73
    • 0037134880 scopus 로고    scopus 로고
    • The First Direct Enantioselective Cross-Aldol Reaction of Aldehydes
    • (b) Northrup, A. B.; MacMillan, D. W. C. The First Direct and Enantioselective Cross-Aldol Reaction of Aldehydes J. Am. Chem. Soc. 2002, 124, 6798-6799.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 6798-6799
    • Northrup, A.B.1    MacMillan, D.W.C.2
  • 74
    • 0037164621 scopus 로고    scopus 로고
    • Proline-Catalyzed Asymmetric Assembly Reactions: Enzyme-like Assembly of Carbohydrates and Polyketides from Three aldehyde Substrates
    • (c) Chowdari, N. S.; Ramachary, D. B.; Córdova, A.; Barbas, C. F., III. Proline-Catalyzed Asymmetric Assembly Reactions: Enzyme-like Assembly of Carbohydrates and Polyketides from Three aldehyde Substrates. Tetrahedron Lett. 2002, 43, 9591-9595.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 9591-9595
    • Chowdari, N.S.1    Ramachary, D.B.2    Córdova, A.3    Barbas III, C.F.4
  • 75
    • 0036927410 scopus 로고    scopus 로고
    • Direct Organocatalytic Aldol Reactions in Buffered Aqueous Media
    • (d) Córdova, A.; Notz, W.; Barbas, C. F., III, Direct Organocatalytic Aldol Reactions in Buffered Aqueous Media. Chem. Commun. 2002, 67, 3024-3025.
    • (2002) Chem. Commun. , vol.67 , pp. 3024-3025
    • Córdova, A.1    Notz, W.2    Barbas III, C.F.3
  • 76
    • 0036260164 scopus 로고    scopus 로고
    • Direct Organo-Catalytic Asymmetric α-Amination of Aldehydes-A Simple Approach to Optically Active α-amino Aldehydes, α-Amino Alcohols, and α-Amino Acids
    • (e) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Direct Organo-Catalytic Asymmetric α-Amination of Aldehydes-A Simple Approach to Optically Active α-amino Aldehydes, α-Amino Alcohols, and α-Amino Acids. Angew. Chem., Int. Ed. 2002, 41, 1790-1793.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 1790-1793
    • Bøgevig, A.1    Juhl, K.2    Kumaragurubaran, N.3    Zhuang, W.4    Jørgensen, K.A.5
  • 77
    • 0037157154 scopus 로고    scopus 로고
    • Direct Catalytic α-Amination of Aldehydes
    • (f) List, B. Direct Catalytic α-Amination of Aldehydes, J. Am. Chem. Soc. 2002, 124, 5656-5657.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 5656-5657
    • List, B.1
  • 79
    • 0034678591 scopus 로고    scopus 로고
    • The Catalytic Asymmetric Aldol Reaction
    • and references therein
    • Machajewski, T. D.; Wong, C.-H. The Catalytic Asymmetric Aldol Reaction. Angew. Chem., Int. Ed. 2000, 39, 1352-1374 and references therein.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 1352-1374
    • Machajewski, T.D.1    Wong, C.-H.2
  • 80
    • 0037028990 scopus 로고    scopus 로고
    • A Highly Enantioselective Route to Either Enantiomer of Both α-and β-Amino Acid Derivatives
    • Córdova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. A Highly Enantioselective Route to Either Enantiomer of Both α-and β-Amino Acid Derivatives. J. Am. Chem. Soc. 2002, 124, 1866-1867.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 1866-1867
    • Córdova, A.1    Watanabe, S.2    Tanaka, F.3    Notz, W.4    Barbas III, C.F.5
  • 81
    • 0037069710 scopus 로고    scopus 로고
    • One-Pot Asymmetric Synthesis of β-Cyanohydroxymethyl α-Amino Acid Derivatives: Formation of Three Contiguous Stereogenic Centers
    • Watanabe, S.-i.; Córdova, A.; Tanaka, F.; Barbas, C. F., III. One-Pot Asymmetric Synthesis of β-Cyanohydroxymethyl α-Amino Acid Derivatives: Formation of Three Contiguous Stereogenic Centers. Org. lett. 2002, 4, 4519-4522.
    • (2002) Org. Lett. , vol.4 , pp. 4519-4522
    • Watanabe, S.-I.1    Córdova, A.2    Tanaka, F.3    Barbas III, C.F.4
  • 82
    • 0037463462 scopus 로고    scopus 로고
    • Direct Organocatalytic Asymmetric Mannich-type Reactions in Aqueous Media: One-Pot Mannich-Allylation Reactions
    • Córdova, A.; Barbas, C. F., III. Direct Organocatalytic Asymmetric Mannich-type Reactions in Aqueous Media: One-Pot Mannich-Allylation Reactions. Tetrahedron Lett. 2003, 44, 1923-1926.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 1923-1926
    • Córdova, A.1    Barbas III, C.F.2
  • 83
    • 24444457925 scopus 로고    scopus 로고
    • Amine-Catalyzed Direct Asymmetric Mannich-type Reactions: Enanioselective Synthesis of Amino acid and Amino Alcohol Derivatives
    • New Orleans, LA, Spring
    • (a) Córdova, A. Amine-Catalyzed Direct Asymmetric Mannich-type Reactions: Enanioselective Synthesis of Amino acid and Amino Alcohol Derivatives. Presented at the 225th ACS National Meeting, New Orleans, LA, Spring 2003.
    • (2003) 225th ACS National Meeting
    • Córdova, A.1
  • 84
    • 4243162724 scopus 로고    scopus 로고
    • One-Pot Direct Organocatalytic Asymmetric Synthesis of γ-Amino Alcohol Derivatives
    • (b) Córdova, A. One-Pot Direct Organocatalytic Asymmetric Synthesis of γ-Amino Alcohol Derivatives. Synlett 2003. 1651-1654.
    • (2003) Synlett , pp. 1651-1654
    • Córdova, A.1
  • 86
    • 1242311795 scopus 로고    scopus 로고
    • note
    • The Mannich adducts are reduced to the more stabile β-amino alcohols prior to isolation and ee determination due to their lower risk of decomposition, epimerization, and racemization.
  • 87
    • 0031030026 scopus 로고    scopus 로고
    • A Highly Stereocontrolled Synthesis of (S)-(-)-3-(4-tert-Butyl)phenyl-1-N-(cis-2,6-dimethyl) morpholinyl-2-methylpropane via Asymmetric Mannich Reaction
    • Vinkovic, V.; Sunjic, V. A Highly Stereocontrolled Synthesis of (S)-(-)-3-(4-tert-Butyl)phenyl-1-N-(cis-2,6-dimethyl) morpholinyl-2-methylpropane via Asymmetric Mannich Reaction. Tetrahedron 1997, 53, 689-696.
    • (1997) Tetrahedron , vol.53 , pp. 689-696
    • Vinkovic, V.1    Sunjic, V.2
  • 88
    • 0037152299 scopus 로고    scopus 로고
    • Anti-Selective SMP-Catalyzed Direct Asymmetric Mannich-type Reactions: Synthesis of Functionalized Amino Acid Derivatives
    • Cørdova, A.; Barbas, C. F., III. Anti-Selective SMP-Catalyzed Direct Asymmetric Mannich-type Reactions: Synthesis of Functionalized Amino Acid Derivatives. Tetrahedron Lett. 2002, 43, 7749-7752.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 7749-7752
    • Cørdova, A.1    Barbas III, C.F.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.