메뉴 건너뛰기




Volumn 39, Issue 10, 2006, Pages 747-760

Predicting the stereochemistry of diphenylphosphino benzoic acid (DPPBA)-based palladium-catalyzed asymmetric allylic alkylation reactions: A working model

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; BENZAMIDE DERIVATIVE; LIGAND; PALLADIUM; PHOSPHINE DERIVATIVE;

EID: 33750620556     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar040063c     Document Type: Article
Times cited : (460)

References (68)
  • 1
    • 0042379988 scopus 로고    scopus 로고
    • Asymmetric Transition-Metal-Catalyzed Allylic Alkylations: Applications in Total Synthesis
    • and earlier citations therein
    • Trost, B. M.; Crawley, M. L. Asymmetric Transition-Metal-Catalyzed Allylic Alkylations: Applications in Total Synthesis. Chem. Rev. 2003, 103, 2921-2944 and earlier citations therein.
    • (2003) Chem. Rev. , vol.103 , pp. 2921-2944
    • Trost, B.M.1    Crawley, M.L.2
  • 2
    • 0033583714 scopus 로고    scopus 로고
    • Regio- and Enantioselective Allylic Alkylation of an Unsymmetrical Substrate: A Working Model
    • Trost, B. M.; Toste, F. D. Regio- and Enantioselective Allylic Alkylation of an Unsymmetrical Substrate: A Working Model. J. Am. Chem. Soc. 1999, 121, 4545-4554.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 4545-4554
    • Trost, B.M.1    Toste, F.D.2
  • 3
    • 1642324310 scopus 로고
    • A Modular Approach for Ligand Design for Asymmetric Allylic Alkylations via Enantioselective Palladium-Catalyzed Ionizations
    • (b) Trost, B. M.; van Vranken, D. L.; Bingel, C. J. A Modular Approach for Ligand Design for Asymmetric Allylic Alkylations via Enantioselective Palladium-Catalyzed Ionizations. J. Am. Chem. Soc. 1992, 114, 9327-9343.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 9327-9343
    • Trost, B.M.1    Van Vranken, D.L.2    Bingel, C.J.3
  • 5
    • 0010990917 scopus 로고
    • New Synthetic Reactions. Stereochemistry of Allylic Alkylation
    • Trost, B. M.; Weber, L. New Synthetic Reactions. Stereochemistry of Allylic Alkylation. J. Am. Chem. Soc. 1975, 97, 1611-1612.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 1611-1612
    • Trost, B.M.1    Weber, L.2
  • 6
    • 0017312351 scopus 로고
    • New Synthetic Reactions. Catalytic vs. Stoichiometric Allylic Alkylation. Stereocontrolled Approach to Steroid Side Chain
    • (b) Trost, B. M.; Verhoeven, T. R. New Synthetic Reactions. Catalytic vs. Stoichiometric Allylic Alkylation. Stereocontrolled Approach to Steroid Side Chain. J. Am. Chem. Soc. 1976, 98, 630-632.
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 630-632
    • Trost, B.M.1    Verhoeven, T.R.2
  • 7
    • 0001611087 scopus 로고
    • Stereochemistry of Oxidative Addition of an Optically Active Allyl Acetate to a Palladium(0) Complex
    • (c) Hayashi, T.; Hagihara, T.; Konishi, M.; Kumada, M. Stereochemistry of Oxidative Addition of an Optically Active Allyl Acetate to a Palladium(0) Complex. J. Am. Chem. Soc. 1983, 105, 7767-7768.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 7767-7768
    • Hayashi, T.1    Hagihara, T.2    Konishi, M.3    Kumada, M.4
  • 8
    • 0000565225 scopus 로고
    • New Method for the Classification of Nucleophiles in the Palladium-Catalyzed Substitution of Allylic Acetates
    • and earlier citations therein
    • (d) Fiaud, J. C.; Legros, L. Y. New Method for the Classification of Nucleophiles in the Palladium-Catalyzed Substitution of Allylic Acetates. J. Org. Chem. 1987, 52, 1907-1911 and earlier citations therein.
    • (1987) J. Org. Chem. , vol.52 , pp. 1907-1911
    • Fiaud, J.C.1    Legros, L.Y.2
  • 9
    • 0026782148 scopus 로고
    • Stereochemistry of the Palladium-Catalyzed Allylic Substitution: The syn-anti Dichotomy in the Formation of (π-Allyl)palladium Complexes and Their Equilibration
    • (e) Stary, I.; Zajicek, J.; Kocovsky, P. Stereochemistry of the Palladium-Catalyzed Allylic Substitution: The syn-anti Dichotomy in the Formation of (π-Allyl)palladium Complexes and Their Equilibration. Tetrahedron 1992, 48, 7229-7250.
    • (1992) Tetrahedron , vol.48 , pp. 7229-7250
    • Stary, I.1    Zajicek, J.2    Kocovsky, P.3
  • 10
    • 0002835977 scopus 로고
    • (π-Allyl)palladium Complexes of Norcamphene. Structure and Reactivity
    • Godleski, S. A. (π-Allyl)palladium Complexes of Norcamphene. Structure and Reactivity. Organometallics 1984, 3, 21-28.
    • (1984) Organometallics , vol.3 , pp. 21-28
    • Godleski, S.A.1
  • 12
    • 0031016772 scopus 로고    scopus 로고
    • A Remarkable Anion Effect on the Enantioselectivity of the Pd-Catalyzed Allylic Amination Using Ferrocenyl Ligands
    • Burkhardt, U.; Baumann, M.; Togni, A. A Remarkable Anion Effect on the Enantioselectivity of the Pd-Catalyzed Allylic Amination Using Ferrocenyl Ligands. Tetrahedron: Asymmetry 1997, 8, 155-159.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 155-159
    • Burkhardt, U.1    Baumann, M.2    Togni, A.3
  • 13
    • 0345306222 scopus 로고    scopus 로고
    • Structural and Kinetic Effects of Chloride Ions in the Palladium-Catalyzed Allylic Substitutions
    • (b) Cantat, T.; Genin, E.; Giroud, C.; Meyer, G.; Jutand, A. Structural and Kinetic Effects of Chloride Ions in the Palladium-Catalyzed Allylic Substitutions. J. Organomet. Chem. 2003, 687, 365-376.
    • (2003) J. Organomet. Chem. , vol.687 , pp. 365-376
    • Cantat, T.1    Genin, E.2    Giroud, C.3    Meyer, G.4    Jutand, A.5
  • 14
    • 0001257521 scopus 로고
    • 3-(1-Acetyl-2,3-dimethylallyl)[(S)-α- phenethylamine]chloropalladium
    • 3-(1-Acetyl-2,3-dimethylallyl)[(S)-α-phenethylamine] chloropalladium. J. Am. Chem. Soc. 1972, 94, 2676-2679.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 2676-2679
    • Faller, J.W.1    Thompson, M.F.2    Tully, M.T.3
  • 15
    • 33845379753 scopus 로고
    • Asymmetric Synthesis. Mechanism of Asymmetric Catalytic Allylation
    • For an example where π-σ-π interconversion occurs at a highly substituted allyl terminus, see Mackenzie, P. B.; Whelan, J.; Bosnich, B. Asymmetric Synthesis. Mechanism of Asymmetric Catalytic Allylation. J. Am. Chem. Soc. 1985, 107, 2046-2054.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 2046-2054
    • Mackenzie, P.B.1    Whelan, J.2    Bosnich, B.3
  • 16
    • 0007682425 scopus 로고
    • Organometallic Conformational Equilibriums. X. Steric Factors and Their Mechanistic Implications in π-Allyl(amine)chloropalladium(II) Complexes
    • Faller, J. W.; Thompson, M. F.; Mattina, M. J. Organometallic Conformational Equilibriums. X. Steric Factors and Their Mechanistic Implications in π-Allyl(amine)chloropalladium(II) Complexes. J. Am. Chem. Soc. 1971, 93, 2642-2653.
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 2642-2653
    • Faller, J.W.1    Thompson, M.F.2    Mattina, M.J.3
  • 17
    • 0032484249 scopus 로고    scopus 로고
    • Mechanistic Implications of the Observation of Kinetic Resolution in a Palladium-Catalyzed Enantioselective Allylic Alkylation
    • For a Pd AAA where nucleophilic attack occurs on a syn,anti complex, see Ramdeehul, S.; Dierkes, P.; Aguado, R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Osborn, J. A. Mechanistic Implications of the Observation of Kinetic Resolution in a Palladium-Catalyzed Enantioselective Allylic Alkylation. Angew. Chem., Int. Ed. 1998, 37, 3118-3121.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 3118-3121
    • Ramdeehul, S.1    Dierkes, P.2    Aguado, R.3    Kamer, P.C.J.4    Van Leeuwen, P.W.N.M.5    Osborn, J.A.6
  • 18
    • 0006989799 scopus 로고    scopus 로고
    • Enanti-oselective Catalysis with Complexes of Asymmetric P,N-Chelate Ligands
    • Helmchen, G.; Kudis, S.; Sennhenn, P.; Steinhagen, H. Enanti-oselective Catalysis with Complexes of Asymmetric P,N-Chelate Ligands. Pure Appl. Chem. 1997, 68, 513-518.
    • (1997) Pure Appl. Chem. , vol.68 , pp. 513-518
    • Helmchen, G.1    Kudis, S.2    Sennhenn, P.3    Steinhagen, H.4
  • 19
    • 5244377546 scopus 로고
    • New Synthetic Reactions. Chemospecificity of Allylic Alkylation
    • Trost, B. M.; Dietsche, T. J.; Fullerton, T. J. New Synthetic Reactions. Chemospecificity of Allylic Alkylation. J. Org. Chem. 1974, 39, 737-738.
    • (1974) J. Org. Chem. , vol.39 , pp. 737-738
    • Trost, B.M.1    Dietsche, T.J.2    Fullerton, T.J.3
  • 20
    • 0000061992 scopus 로고
    • 3-Neryl)palladium complexes. Evidence for Electronic Control of the Regiochemistry of Nucleophilic Addition
    • 3-Neryl)palladium complexes. Evidence for Electronic Control of the Regiochemistry of Nucleophilic Addition. Organometallics 1985, 4, 1275-1283.
    • (1985) Organometallics , vol.4 , pp. 1275-1283
    • Akermark, B.1    Vitagliano, A.2
  • 21
    • 0033949478 scopus 로고    scopus 로고
    • Phosphinooxazolines - A New Class of Versatile, Modular P,N-Ligands for Asymmetric Catalysis
    • (b) Helmchen, G.; Pfaltz, A. Phosphinooxazolines - A New Class of Versatile, Modular P,N-Ligands for Asymmetric Catalysis. Acc. Chem. Res. 2000, 33, 336-345.
    • (2000) Acc. Chem. Res. , vol.33 , pp. 336-345
    • Helmchen, G.1    Pfaltz, A.2
  • 22
    • 0002299713 scopus 로고    scopus 로고
    • Regio- and Enantio-selective Allylic Alkylation Catalysed by a Chiral Monophosphine-Palladium Complex
    • (c) Hayashi, T.; Kawatsura, M.; Uozumi, Y. Regio- and Enantio-selective Allylic Alkylation Catalysed by a Chiral Monophosphine-Palladium Complex. Chem. Commun. 1997, 561-562.
    • (1997) Chem. Commun. , pp. 561-562
    • Hayashi, T.1    Kawatsura, M.2    Uozumi, Y.3
  • 24
    • 84989591506 scopus 로고
    • 2 Symmetrical Bis(aziridine) Preparation and NMR Spectroscopic Investigation of a Chiral π-Allyl Species
    • 2 Symmetrical Bis(aziridine) Preparation and NMR Spectroscopic Investigation of a Chiral π-Allyl Species. Chem. - Eur. J. 1995, 1, 12-16.
    • (1995) Chem. - Eur. J. , vol.1 , pp. 12-16
    • Andersson, P.G.1    Harden, A.2    Tanner, D.3    Norrby, P.D.4
  • 25
    • 3242857105 scopus 로고
    • Chiral Semicorrins and Related Nitrogen Heterocycles as Ligands in Asymmetric Catalysis
    • Pfaltz, A. Chiral Semicorrins and Related Nitrogen Heterocycles as Ligands in Asymmetric Catalysis. Acc. Chem. Res. 1993, 26, 339-345.
    • (1993) Acc. Chem. Res. , vol.26 , pp. 339-345
    • Pfaltz, A.1
  • 26
    • 0001638084 scopus 로고
    • Modification of Optically Active Ferrocenylphosphine Ligands for Palladium-Catalyzed Asymmetric Allylic Alkylation
    • Hayashi, T.; Yamamoto, A.; Ito, Y.; Hagihara, T. Modification of Optically Active Ferrocenylphosphine Ligands for Palladium-Catalyzed Asymmetric Allylic Alkylation. Tetrahedron Lett. 1986, 27, 191-194.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 191-194
    • Hayashi, T.1    Yamamoto, A.2    Ito, Y.3    Hagihara, T.4
  • 27
    • 0000345787 scopus 로고
    • A Novel Easily Accessible Chiral Ferrocenyldiphosphine for Highly Enantioselective Hydrogenation, Allylic Alkylation, and Hydroboration Reactions
    • Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. A Novel Easily Accessible Chiral Ferrocenyldiphosphine for Highly Enantioselective Hydrogenation, Allylic Alkylation, and Hydroboration Reactions. J. Am. Chem. Soc. 1994, 116, 4062-4066.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 4062-4066
    • Togni, A.1    Breutel, C.2    Schnyder, A.3    Spindler, F.4    Landert, H.5    Tijani, A.6
  • 28
    • 0034706036 scopus 로고    scopus 로고
    • Application of Chiral Mixed Phosphorus/Sulfur Ligands to Palladium-Catalyzed Allylic Substitutions
    • Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagne, M. R. Application of Chiral Mixed Phosphorus/Sulfur Ligands to Palladium-Catalyzed Allylic Substitutions. J. Am. Chem. Soc. 2000, 122, 7905-7920.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 7905-7920
    • Evans, D.A.1    Campos, K.R.2    Tedrow, J.S.3    Michael, F.E.4    Gagne, M.R.5
  • 29
    • 0033754673 scopus 로고    scopus 로고
    • Asymmetric Synthesis of Novel Ferrocenyl Ligands with Planar and Central Chirality and Their Application to Pd-Catalyzed Allylic Substitutions
    • (b) Enders, D.; Peters, R.; Lochtman, R.; Raabe, G.; Runsink, J.; Bats, J. W. Asymmetric Synthesis of Novel Ferrocenyl Ligands with Planar and Central Chirality and Their Application to Pd-Catalyzed Allylic Substitutions. Eur. J. Org. Chem. 2000, 3399-3426.
    • (2000) Eur. J. Org. Chem. , pp. 3399-3426
    • Enders, D.1    Peters, R.2    Lochtman, R.3    Raabe, G.4    Runsink, J.5    Bats, J.W.6
  • 30
    • 27144508180 scopus 로고    scopus 로고
    • Regioselectivity in the Palladium/(S)BINAP(S)-Catalyzed Asymmetric Allylic Amination: Reaction Scope, Kinetics, and Stereodynamics
    • (c) Faller, J. W.; Wilt, J. C. Regioselectivity in the Palladium/(S)BINAP(S)-Catalyzed Asymmetric Allylic Amination: Reaction Scope, Kinetics, and Stereodynamics. Organometallics 2005, 24, 5076-5083.
    • (2005) Organometallics , vol.24 , pp. 5076-5083
    • Faller, J.W.1    Wilt, J.C.2
  • 31
    • 0037414501 scopus 로고    scopus 로고
    • 1-Phosphino-2-sulfenylferrocenes as Planar Chiral Ligands in Enantioselective Palladium-Catalyzed Allylic Substitutions
    • (d) Mancheno, O. G.; Priego, J.; Cabrera, S.; Arrayas, R. G.; Llamas, T.; Carretero, J. C. 1-Phosphino-2-sulfenylferrocenes as Planar Chiral Ligands in Enantioselective Palladium-Catalyzed Allylic Substitutions. J. Org. Chem. 2003, 68, 3679-3686.
    • (2003) J. Org. Chem. , vol.68 , pp. 3679-3686
    • Mancheno, O.G.1    Priego, J.2    Cabrera, S.3    Arrayas, R.G.4    Llamas, T.5    Carretero, J.C.6
  • 32
    • 0028349296 scopus 로고
    • Catalysis of Allylic Substitutions by Pd Complexes of Oxazolines Containing an Additional P, S, or Se Center. X-ray Crystal Structures and Solution Structures of Chiral π-Allyl Palladium Complexes of Phosphinoaryloxazolines
    • Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelin, M.; Huttner, G.; Walter, O.; Zsolnai, L. Catalysis of Allylic Substitutions by Pd Complexes of Oxazolines Containing an Additional P, S, or Se Center. X-ray Crystal Structures and Solution Structures of Chiral π-Allyl Palladium Complexes of Phosphinoaryloxazolines. Tetrahedron Lett. 1994, 35, 1523-1526.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 1523-1526
    • Sprinz, J.1    Kiefer, M.2    Helmchen, G.3    Reggelin, M.4    Huttner, G.5    Walter, O.6    Zsolnai, L.7
  • 33
    • 0000273585 scopus 로고    scopus 로고
    • The Ups and Downs of Allylpalladium Complexes in Catalysis
    • (b) Williams, J. M. J. The Ups and Downs of Allylpalladium Complexes in Catalysis. Synlett 1996, 705-710.
    • (1996) Synlett , pp. 705-710
    • Williams, J.M.J.1
  • 34
    • 33750614009 scopus 로고    scopus 로고
    • See also ref 13b
    • (c) See also ref 13b.
  • 35
    • 4243434656 scopus 로고
    • Coordination Chemistry of Thioethers, Selenoethers, and Telluroethers in Transition-Metal Complexes
    • Murray, S.; Hartley, F. Coordination Chemistry of Thioethers, Selenoethers, and Telluroethers in Transition-Metal Complexes. Chem. Rev. 1981, 87, 365-414.
    • (1981) Chem. Rev. , vol.87 , pp. 365-414
    • Murray, S.1    Hartley, F.2
  • 36
    • 0000390005 scopus 로고    scopus 로고
    • 2 Symmetric Semicorrins and Bisoxazolines to Non-symmetric Phosphinooxazolines
    • 2 Symmetric Semicorrins and Bisoxazolines to Non-symmetric Phosphinooxazolines. Acta Chem. Scand. 1996, 50, 189-194.
    • (1996) Acta Chem. Scand. , vol.50 , pp. 189-194
    • Pfaltz, A.1
  • 37
    • 1542745046 scopus 로고    scopus 로고
    • Chiral Thioimidazoline Ligands for Palladium-Catalyzed Asymmetric Allylation
    • (c) Morimoto, T.; Tachibana, K.; Achiwa, K. Chiral Thioimidazoline Ligands for Palladium-Catalyzed Asymmetric Allylation. Synlett 1997, 783-785.
    • (1997) Synlett , pp. 783-785
    • Morimoto, T.1    Tachibana, K.2    Achiwa, K.3
  • 38
    • 0001326728 scopus 로고    scopus 로고
    • Catalytic Asymmetric Reactions via π-Allylpalladium Complexes Coordinated with Chiral Monophosphine Ligands
    • (d) Hayashi, T. Catalytic Asymmetric Reactions via π-Allylpalladium Complexes Coordinated with Chiral Monophosphine Ligands. J. Organomet. Chem. 1999, 576, 195-202.
    • (1999) J. Organomet. Chem. , vol.576 , pp. 195-202
    • Hayashi, T.1
  • 39
    • 0036976628 scopus 로고    scopus 로고
    • Asymmetric Catalysis Using Planar Chiral Arene Chromium Complexes
    • (e) Gibson, S. E.; Ibrahim, H. Asymmetric Catalysis Using Planar Chiral Arene Chromium Complexes. Chem. Commun. 2002, 21, 2465-2473.
    • (2002) Chem. Commun. , vol.21 , pp. 2465-2473
    • Gibson, S.E.1    Ibrahim, H.2
  • 40
    • 0242713084 scopus 로고    scopus 로고
    • Partially Hydrogenated 1,1′-Binaphthyl as Ligand Scaffold in Metal-Catalyzed Asymmetric Synthesis
    • (f) Au-Yeung, T. T. L.; Chan, S. S.; Chan, A. S. C. Partially Hydrogenated 1,1′-Binaphthyl as Ligand Scaffold in Metal-Catalyzed Asymmetric Synthesis. Adv. Synth. Catal. 2003, 345, 537-555.
    • (2003) Adv. Synth. Catal. , vol.345 , pp. 537-555
    • Au-Yeung, T.T.L.1    Chan, S.S.2    Chan, A.S.C.3
  • 41
    • 0348224187 scopus 로고    scopus 로고
    • Chiral Tetraaza Ligands in Asymmetric Catalysis: Recent Progress
    • (g) Fonseca, M. H.; Koenig, B. Chiral Tetraaza Ligands in Asymmetric Catalysis: Recent Progress. Adv. Synth. Catal. 2003, 345, 1173-1185.
    • (2003) Adv. Synth. Catal. , vol.345 , pp. 1173-1185
    • Fonseca, M.H.1    Koenig, B.2
  • 42
    • 33750617677 scopus 로고    scopus 로고
    • note
    • When ionization forms a meso-allyl unit, the enantioselectivity is determined at the nucleophilic addition stage.
  • 43
    • 0036371962 scopus 로고    scopus 로고
    • Pd Asymmetric Allylic Alkylation (AAA). A Powerful Synthetic Tool
    • Trost, B. M. Pd Asymmetric Allylic Alkylation (AAA). A Powerful Synthetic Tool. Chem. Pharm. Bull. 2002, 50, 1-14.
    • (2002) Chem. Pharm. Bull. , vol.50 , pp. 1-14
    • Trost, B.M.1
  • 44
    • 33748741518 scopus 로고
    • A New Platform for Designing Ligands for Asymmetric Induction in Allylic Alkylations
    • Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. A New Platform for Designing Ligands for Asymmetric Induction in Allylic Alkylations. Angew. Chem., Int. Ed. Engl. 1995, 34, 2386-2388.
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 2386-2388
    • Trost, B.M.1    Breit, B.2    Peukert, S.3    Zambrano, J.4    Ziller, J.W.5
  • 45
    • 85047695069 scopus 로고    scopus 로고
    • Application of the AAA Reaction to the Synthesis of the Furanoside of C-2-epi-Hygromycin A: A Total Synthesis of C-2-epi-Hygromycin A
    • Trost, B. M.; Dudash, J., Jr.; Dirat, O. Application of the AAA Reaction to the Synthesis of the Furanoside of C-2-epi-Hygromycin A: A Total Synthesis of C-2-epi-Hygromycin A. Chem. - Eur. J. 2002, 8, 259-268.
    • (2002) Chem. - Eur. J. , vol.8 , pp. 259-268
    • Trost, B.M.1    Dudash Jr., J.2    Dirat, O.3
  • 46
    • 0000455625 scopus 로고    scopus 로고
    • Enhanced Enantioselectivity in the Desymmetrization of meso-Biscarbamates
    • Trost, B. M.; Patterson, D. E. Enhanced Enantioselectivity in the Desymmetrization of meso-Biscarbamates. J. Org. Chem. 1998, 63, 1339-1341.
    • (1998) J. Org. Chem. , vol.63 , pp. 1339-1341
    • Trost, B.M.1    Patterson, D.E.2
  • 47
    • 0032527965 scopus 로고    scopus 로고
    • A New Strategy for the Synthesis of Sphingosine Analogues. Sphingofungin F
    • Trost, B. M.; Lee, C. B. A New Strategy for the Synthesis of Sphingosine Analogues. Sphingofungin F. J. Am. Chem. Soc. 1998, 120, 6818-6819.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 6818-6819
    • Trost, B.M.1    Lee, C.B.2
  • 48
    • 0034725392 scopus 로고    scopus 로고
    • α-Acetoxysulfones as "Chiral Aldehyde" Equivalents
    • (b) Trost, B. M.; Crawley, M. L.; Lee, C. B. α-Acetoxysulfones as "Chiral Aldehyde" Equivalents. J. Am. Chem. Soc. 2000, 122, 6120-6121,
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 6120-6121
    • Trost, B.M.1    Crawley, M.L.2    Lee, C.B.3
  • 49
    • 0034826477 scopus 로고    scopus 로고
    • Geminal Dicarboxylates as Carbonyl Surrogates for Asymmetric Synthesis. Part II. Scope and Applications
    • and earlier citations therein
    • (c) Trost, B. M.; Lee, C. B. Geminal Dicarboxylates as Carbonyl Surrogates for Asymmetric Synthesis. Part II. Scope and Applications. J. Am. Chem. Soc. 2001, 123, 3687-3696 and earlier citations therein.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 3687-3696
    • Trost, B.M.1    Lee, C.B.2
  • 50
    • 0037122149 scopus 로고    scopus 로고
    • An Efficient One-Pot Enantio- and Diastereoselective Synthesis of Heterocycles
    • Trost, B. M.; Machacek, M. R. An Efficient One-Pot Enantio- and Diastereoselective Synthesis of Heterocycles. Angew. Chem., Int. Ed. 2002, 41, 4693-4697.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 4693-4697
    • Trost, B.M.1    Machacek, M.R.2
  • 51
    • 0000547520 scopus 로고
    • Palladium-Catalyzed Exchange of Allylic Groups of Ethers and Esters with Active Hydrogen Compounds. II
    • Takahashi, K.; Miyake, A.; Hata, G. Palladium-Catalyzed Exchange of Allylic Groups of Ethers and Esters with Active Hydrogen Compounds. II. Bull. Chem. Soc. Jpn. 1972, 45, 230-236.
    • (1972) Bull. Chem. Soc. Jpn. , vol.45 , pp. 230-236
    • Takahashi, K.1    Miyake, A.2    Hata, G.3
  • 52
    • 0001582458 scopus 로고
    • Alkoxides as Nucleophiles in (π-Allyl)palladium Chemistry. Synthetic and Mechanistic Studies
    • (b) Santon, S. A.; Felman, S. W.; Parkhurst, C. S.; Godleski, S. A. Alkoxides as Nucleophiles in (π-Allyl)palladium Chemistry. Synthetic and Mechanistic Studies. J. Am. Chem. Soc. 1983, 105, 1964-1969.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 1964-1969
    • Santon, S.A.1    Felman, S.W.2    Parkhurst, C.S.3    Godleski, S.A.4
  • 53
    • 0042709607 scopus 로고    scopus 로고
    • Unusual Effects in the Pd-Catalyzed Asymmetric Allylic Alkylations: Synthesis of Chiral Chromans
    • Trost, B. M.; Shen, H. C.; Dong, L.; Surivet, J. P. Unusual Effects in the Pd-Catalyzed Asymmetric Allylic Alkylations: Synthesis of Chiral Chromans. J. Am. Chem. Soc. 2003, 125, 9276-9277.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 9276-9277
    • Trost, B.M.1    Shen, H.C.2    Dong, L.3    Surivet, J.P.4
  • 54
    • 0035901655 scopus 로고    scopus 로고
    • Asymmetric Induction of Conduritols via AAA Reactions: Synthesis of the Aminocyclohexitol of Hygromycin A
    • and earlier citations therein
    • Trost, B. M.; Dudash, J., Jr.; Hembre, E. J. Asymmetric Induction of Conduritols via AAA Reactions: Synthesis of the Aminocyclohexitol of Hygromycin A. Chem. - Eur. J. 2001, 7, 1619-1629 and earlier citations therein.
    • (2001) Chem. - Eur. J. , vol.7 , pp. 1619-1629
    • Trost, B.M.1    Dudash Jr., J.2    Hembre, E.J.3
  • 56
    • 0034725412 scopus 로고    scopus 로고
    • Dynamic Kinetic Asymmetric Transformation of Diene Monoepoxides: A Practical Asymmetric Synthesis of Vinylglycinol, Vigabatrin, and Ethambutol
    • Trost, B. M.; Bunt, R. C.; Lemoine, R. C.; Calkins, T. L. Dynamic Kinetic Asymmetric Transformation of Diene Monoepoxides: A Practical Asymmetric Synthesis of Vinylglycinol, Vigabatrin, and Ethambutol. J. Am. Chem. Soc. 2000, 122, 5968-5976.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 5968-5976
    • Trost, B.M.1    Bunt, R.C.2    Lemoine, R.C.3    Calkins, T.L.4
  • 57
    • 0033595445 scopus 로고    scopus 로고
    • Inorganic Carbonates as Nucleophiles for the Asymmetric Synthesis of Vinylglycidols
    • and earlier citations therein
    • Trost, B. M.; McEachern, E. J. Inorganic Carbonates as Nucleophiles for the Asymmetric Synthesis of Vinylglycidols. J. Am. Chem. Soc. 1999, 121, 8649-8650 and earlier citations therein.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 8649-8650
    • Trost, B.M.1    McEachern, E.J.2
  • 58
    • 0035909604 scopus 로고    scopus 로고
    • An Enantioselective Strategy to Macrocyclic Bisindolylmaleimides. An Efficient Formal Synthesis of LY 333531
    • (b) Trost, B. M.; Tang, W. An Enantioselective Strategy to Macrocyclic Bisindolylmaleimides. An Efficient Formal Synthesis of LY 333531. Org. Lett. 2001, 3, 3409-3411.
    • (2001) Org. Lett. , vol.3 , pp. 3409-3411
    • Trost, B.M.1    Tang, W.2
  • 59
    • 0034649735 scopus 로고    scopus 로고
    • Asymmetric Synthesis of Quaternary Centers. Total Synthesis of (-)-Malyngolide
    • (c) Trost, B. M.; Tang, W.; Schulte, J. L. Asymmetric Synthesis of Quaternary Centers. Total Synthesis of (-)-Malyngolide. Org. Lett. 2000, 2, 4013-4015.
    • (2000) Org. Lett. , vol.2 , pp. 4013-4015
    • Trost, B.M.1    Tang, W.2    Schulte, J.L.3
  • 60
    • 0035956545 scopus 로고    scopus 로고
    • Atom Economic Asymmetric Creation of Quaternary Carbon: Regio- and Enantioselective Reactions of a Vinylepoxide with a Carbon Nucleophile
    • Trost, B. M.; Jiang, C. Atom Economic Asymmetric Creation of Quaternary Carbon: Regio- and Enantioselective Reactions of a Vinylepoxide with a Carbon Nucleophile. J. Am. Chem. Soc. 2001, 123, 12907-12908.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 12907-12908
    • Trost, B.M.1    Jiang, C.2
  • 62
    • 0037119732 scopus 로고    scopus 로고
    • Palladium-Catalyzed Asymmetric Allylic Alkylation of α-Aryl Ketones
    • (b) Trost, B. M.; Schroeder, G. M.; Kristesen, J. Palladium-Catalyzed Asymmetric Allylic Alkylation of α-Aryl Ketones. Angew. Chem., Int. Ed. 2002, 47, 3492-3495.
    • (2002) Angew. Chem., Int. Ed. , vol.47 , pp. 3492-3495
    • Trost, B.M.1    Schroeder, G.M.2    Kristesen, J.3
  • 63
    • 0034629278 scopus 로고    scopus 로고
    • Palladium-Catalyzed Asymmetric Allylic Alkylation of Barbituric Acid Derivatives: Enantioselective Syntheses of Cyclopentobarbital and Pentobarbital
    • (c) Trost, B. M.; Schroeder, G. M. Palladium-Catalyzed Asymmetric Allylic Alkylation of Barbituric Acid Derivatives: Enantioselective Syntheses of Cyclopentobarbital and Pentobarbital. J. Org. Chem. 2000, 65, 1569-1573.
    • (2000) J. Org. Chem. , vol.65 , pp. 1569-1573
    • Trost, B.M.1    Schroeder, G.M.2
  • 64
    • 0033591944 scopus 로고    scopus 로고
    • Palladium-Catalyzed Asymmetric Alkylation of Ketone Enolates
    • Trost, B. M.; Schroeder, G. M. Palladium-Catalyzed Asymmetric Alkylation of Ketone Enolates. J. Am. Chem. Soc. 1999, 121, 6759-6760.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 6759-6760
    • Trost, B.M.1    Schroeder, G.M.2
  • 65
    • 0034669655 scopus 로고    scopus 로고
    • Enantioselective Total Synthesis of (-)-Galanthamine
    • Trost, B. M.; Toste, F. D. Enantioselective Total Synthesis of (-)-Galanthamine. J. Am. Chem. Soc. 2000, 122, 11262-11263.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 11262-11263
    • Trost, B.M.1    Toste, F.D.2
  • 68
    • 0037019541 scopus 로고    scopus 로고
    • Callipeltoside A: Total Synthesis, Assignment of the Absolute and Relative Configuration, and Evaluation of Synthetic Analogues
    • Trost, B. M.; Gunzner, J. L.; Dirat, O.; Rhee, Y. H. Callipeltoside A: Total Synthesis, Assignment of the Absolute and Relative Configuration, and Evaluation of Synthetic Analogues. J. Am. Chem. Soc. 2002, 124, 10396-10415.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 10396-10415
    • Trost, B.M.1    Gunzner, J.L.2    Dirat, O.3    Rhee, Y.H.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.