메뉴 건너뛰기




Volumn 33, Issue 6, 2000, Pages 412-420

Enantioselective nucleophilic catalysis with 'planar-chiral' heterocycles

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; FERROUS ION; HETEROCYCLIC COMPOUND; KETENE DERIVATIVE; KETONE; LACTONE DERIVATIVE;

EID: 0033921576     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar990077w     Document Type: Article
Times cited : (453)

References (55)
  • 2
    • 0002842478 scopus 로고
    • Hypernucleophilic acylation catalysts. II. Simple preparation of acyl-5-oxazolinones from 5-acyloxyoxazoles
    • Steglich, W.; Höfle, G. Hypernucleophilic Acylation Catalysts. II. Simple Preparation of Acyl-5-oxazolinones from 5-Acyloxyoxazoles. Tetrahedron Lett. 1970, 4727-4730.
    • (1970) Tetrahedron Lett. , pp. 4727-4730
    • Steglich, W.1    Höfle, G.2
  • 3
    • 84903751002 scopus 로고
    • Ueber quantitative esterbildung und bestimmung von alkoholen resp. phenolen
    • (a) Pyridine: Verley, A.; Bolsing, F. Ueber Quantitative Esterbildung und Bestimmung von Alkoholen resp. Phenolen. Ber. Dtsch. Chem. Ges. 1901, 34, 3354-3358.
    • (1901) Ber. Dtsch. Chem. Ges. , vol.34 , pp. 3354-3358
    • Verley, A.1    Bolsing, F.2
  • 4
    • 84981783095 scopus 로고
    • 4-Dimethylaminopyridine: N,N-dimethyl-4-pyridinamine, a very effective acylation catalyst
    • (b) 4-Dimethylaminopyridine: N,N-Dimethyl-4-pyridinamine, A Very Effective Acylation Catalyst. Steglich, W.; Höfle, G. Angew. Chem., Int. Ed. Engl. 1969, 8, 981. See also: Litvinenko, L. M.; Kirichenko, A. I. Basicity and Stereospecificity in Nucleophilic Catalysis by Tertiary Amines. Dokl. Akad. Nauk SSSR Ser. Khim. 1967, 176, 97-100.
    • (1969) Angew. Chem., Int. Ed. Engl. , vol.8 , pp. 981
    • Steglich, W.1    Höfle, G.2
  • 5
    • 0002244727 scopus 로고
    • Basicity and stereospecificity in nucleophilic catalysis by tertiary amines
    • (b) 4-Dimethylaminopyridine: N,N-Dimethyl-4-pyridinamine, A Very Effective Acylation Catalyst. Steglich, W.; Höfle, G. Angew. Chem., Int. Ed. Engl. 1969, 8, 981. See also: Litvinenko, L. M.; Kirichenko, A. I. Basicity and Stereospecificity in Nucleophilic Catalysis by Tertiary Amines. Dokl. Akad. Nauk SSSR Ser. Khim. 1967, 176, 97-100.
    • (1967) Dokl. Akad. Nauk SSSR Ser. Khim. , vol.176 , pp. 97-100
    • Litvinenko, L.M.1    Kirichenko, A.I.2
  • 6
    • 37049106282 scopus 로고
    • 4-Dialkylaminopyridines: Super acylation and alkylation catalysts
    • For reviews, see: (a) Scriven, E. F. V. 4-Dialkylaminopyridines: Super Acylation and Alkylation Catalysts. Chem. Soc. Rev. 1983, 12, 129-161.
    • (1983) Chem. Soc. Rev. , vol.12 , pp. 129-161
    • Scriven, E.F.V.1
  • 7
    • 0001557720 scopus 로고
    • Aminopyridines as acylation catalysts for tertiary alcohols
    • (b) Hassner, A.; Krepski, L R.; Alexanian, V. Aminopyridines as Acylation Catalysts for Tertiary Alcohols. Tetrahedron 1978, 34, 2069-2076.
    • (1978) Tetrahedron , vol.34 , pp. 2069-2076
    • Hassner, A.1    Krepski, L.R.2    Alexanian, V.3
  • 9
    • 0029876822 scopus 로고    scopus 로고
    • Kinetic resolution of secondary alcohols. Enantioselective acylation mediated by a chiral (Dimethylamino)pyridine derivative
    • For a chiral derivative of DMAP that has been used as a very effective stoichiometric chiral acylating reagent, see: Vedejs, E.; Chen, X. Kinetic Resolution of Secondary Alcohols. Enantioselective Acylation Mediated by a Chiral (Dimethylamino)pyridine Derivative. J. Am. Chem. Soc. 1996, 118, 1809-1810.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 1809-1810
    • Vedejs, E.1    Chen, X.2
  • 10
    • 0003116430 scopus 로고
    • Planar chiral molecular structures
    • (a) Schlögl, K. Planar Chiral Molecular Structures. Top. Curr. Chem. 1984, 125, 29-62.
    • (1984) Top. Curr. Chem. , vol.125 , pp. 29-62
    • Schlögl, K.1
  • 12
    • 0032486788 scopus 로고    scopus 로고
    • Nucleophilic catalysis with π-bound nitrogen heterocycles: Synthesis of the first ruthenium catalysts and comparison of the reactivity and the enantioselectivity of ruthenium and iron complexes
    • For a study of the corresponding RuCp' complexes, see: Garrett, C. E.; Lo, M. M.-C.; Fu, G. C. Nucleophilic Catalysis with π-Bound Nitrogen Heterocycles: Synthesis of the First Ruthenium Catalysts and Comparison of the Reactivity and the Enantioselectivity of Ruthenium and Iron Complexes. J. Am. Chem. Soc. 1998, 120, 7479-7483.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 7479-7483
    • Garrett, C.E.1    Lo, M.M.-C.2    Fu, G.C.3
  • 13
    • 33947491077 scopus 로고
    • Organometallic chemistry of the transition metals. VIII. π-cyclopentadienyl-π-pyrrolyliron and π-cyclopentadienyl-π-indenyliron
    • For early work on azaferrocenes, see: (a) King, R. B.; Bisnette, M. B. Organometallic Chemistry of the Transition Metals. VIII. π-Cyclopentadienyl-π-pyrrolyliron and π-Cyclopentadienyl-π-indenyliron. Inorg. Chem. 1964, 3, 796-800.
    • (1964) Inorg. Chem. , vol.3 , pp. 796-800
    • King, R.B.1    Bisnette, M.B.2
  • 15
    • 0001408130 scopus 로고
    • Organometallic complexes of heterocycles. I. σ,π-complexes of five-membered monoheterocycles
    • For reviews that include overviews of azaferrocene chemistry, see: (a) Sadimenko, A. P.; Garnovskii, A. D.; Retta, N. Organometallic Complexes of Heterocycles. I. σ,π-Complexes of Five-membered Monoheterocycles. Coord. Chem. Rev. 1993, 126, 237-318.
    • (1993) Coord. Chem. Rev. , vol.126 , pp. 237-318
    • Sadimenko, A.P.1    Garnovskii, A.D.2    Retta, N.3
  • 16
    • 0000274338 scopus 로고
    • Reactions of the η5-pyrrolyl ligand: A new challenge in the chemistry of pyrroles
    • (b) Zakrzewski, J. Reactions of the η5-Pyrrolyl Ligand: A New Challenge in the Chemistry of Pyrroles. Heterocycles 1990, 31, 383-396.
    • (1990) Heterocycles , vol.31 , pp. 383-396
    • Zakrzewski, J.1
  • 17
    • 84988141845 scopus 로고
    • Pyrroles and related systems as π-ligands in coordination chemistry
    • (c) Kuhn, N. Pyrroles and Related Systems as π-Ligands in Coordination Chemistry. Bull. Soc. Chim. Belg. 1990, 99, 707-715.
    • (1990) Bull. Soc. Chim. Belg. , vol.99 , pp. 707-715
    • Kuhn, N.1
  • 18
    • 0342714990 scopus 로고    scopus 로고
    • note
    • (a) For a report of N-alkylation of azaferrocene with methyl iodide, see ref 8b.
  • 19
    • 0000661210 scopus 로고
    • Heterocycles as ligands. V. Synthesis and characterization of 2,3,4,5-tetramethyl-1-azaferrocene
    • (b) For a report of N-acylation of 2,3,4,5-tetramethyl-azaferrocene with acetyl chloride, see: Kuhn, N.; Schulten, M.; Zauder, E.; Augart, N.; Boese, R. Heterocycles as Ligands. V. Synthesis and Characterization of 2,3,4,5-Tetramethyl-1-azaferrocene. Chem. Ber. 1989, 122, 1891-1896.
    • (1989) Chem. Ber. , vol.122 , pp. 1891-1896
    • Kuhn, N.1    Schulten, M.2    Zauder, E.3    Augart, N.4    Boese, R.5
  • 21
    • 84981769685 scopus 로고
    • Optically active 2-methylazaferrocene
    • Optically active 2-methylazaferrocene has been prepared through classical resolution (the level of enantiomeric purity was not determined): Bauer, K.; Falk, H.; Schlögl, K. Optically Active 2-Methylazaferrocene. Angew. Chem., Int. Ed. Engl. 1969, 8, 135.
    • (1969) Angew. Chem., Int. Ed. Engl. , vol.8 , pp. 135
    • Bauer, K.1    Falk, H.2    Schlögl, K.3
  • 22
    • 0000114544 scopus 로고    scopus 로고
    • Chiral π-complexes of heterocycles with transition metals: A versatile new family of nucleophilic catalysts
    • Ruble, J. C.; Fu, G. C. Chiral π-Complexes of Heterocycles with Transition Metals: A Versatile New Family of Nucleophilic Catalysts. J. Org. Chem. 1996, 61, 7230-7231.
    • (1996) J. Org. Chem. , vol.61 , pp. 7230-7231
    • Ruble, J.C.1    Fu, G.C.2
  • 23
    • 0017387938 scopus 로고
    • Synthesis of antibacterial p-quinols from marine sponges. Synthetic applications of "masked" quinones
    • (a) Evans, D. A.; Wong, R. Y. Synthesis of Antibacterial p-Quinols from Marine Sponges. Synthetic Applications of "Masked" Quinones. J. Org. Chem. 1977, 42, 350-352.
    • (1977) J. Org. Chem , vol.42 , pp. 350-352
    • Evans, D.A.1    Wong, R.Y.2
  • 24
    • 0001661818 scopus 로고
    • A facile synthesis of cyanohydrin trimethylsilyl ethers by the addition reaction of trimethylsilyl cyanide with aldehydes under basic condition
    • (b) Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. A Facile Synthesis of Cyanohydrin Trimethylsilyl Ethers by the Addition Reaction of Trimethylsilyl Cyanide with Aldehydes Under Basic Condition. Chem. Lett. 1991, 537-540.
    • (1991) Chem. Lett. , pp. 537-540
    • Tsuchiya, Y.1    Mukaiyama, T.2
  • 25
    • 0342279973 scopus 로고    scopus 로고
    • Ph. D. thesis, Massachusetts Institute of Technology
    • Ruble, J. C. Ph. D. thesis, Massachusetts Institute of Technology, 1999.
    • (1999)
    • Ruble, J.C.1
  • 26
    • 0033599548 scopus 로고    scopus 로고
    • Enantioselective addition of alcohols to ketenes catalyzed by a planar-chiral azaferrocene: Catalytic asymmetric synthesis of arylpropionic acids
    • Hodous, B. L.; Ruble, J. C.; Fu, G. C. Enantioselective Addition of Alcohols to Ketenes Catalyzed by a Planar-Chiral Azaferrocene: Catalytic Asymmetric Synthesis of Arylpropionic Acids. J. Am. Chem. Soc. 1999, 121, 2637-2638.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 2637-2638
    • Hodous, B.L.1    Ruble, J.C.2    Fu, G.C.3
  • 27
    • 84982337484 scopus 로고
    • Asymmetrische synthesen mit ketenen. I. Alkaloid-katalysierte asymmetrische synthesen von α-phenyl-propion-säureestern
    • (a) Pracejus, H. Asymmetrische Synthesen mit Ketenen. I. Alkaloid-katalysierte Asymmetrische Synthesen von α-Phenyl-propion-säureestern. Justus Liebigs Ann. Chem. 1960, 634, 9-22.
    • (1960) Justus Liebigs Ann. Chem. , vol.634 , pp. 9-22
    • Pracejus, H.1
  • 28
    • 84982058692 scopus 로고
    • Asymmetrische synthesen mit ketenen. II. Stereospezifische addition von α-phenyl-äthylamin an phenyl-methyl-keten
    • (b) Pracejus, H. Asymmetrische Synthesen mit Ketenen. II. Stereospezifische Addition von α-Phenyl-äthylamin an Phenyl-methyl-keten. Justus Liebigs Ann. Chem. 1960, 634, 23-29.
    • (1960) Justus Liebigs Ann. Chem. , vol.634 , pp. 23-29
    • Pracejus, H.1
  • 29
    • 0001213707 scopus 로고
    • Über den lösungsmitteleinfluss auf den sterischen ablauf zweier asymmetrischer amidsynthesen
    • (c) Pracejus, H.; Tille, A. Über den Lösungsmitteleinfluss auf den Sterischen Ablauf Zweier Asymmetrischer Amidsynthesen. Chem. Ber. 1963, 96, 854-865.
    • (1963) Chem. Ber. , vol.96 , pp. 854-865
    • Pracejus, H.1    Tille, A.2
  • 30
    • 0000475490 scopus 로고
    • Zusammenhänge zwischen dem räumlichen bau einiger alkaloidartiger katalysatoren und ihren stereospezifischen wirkungen bei asymmetrischen estersynthesen
    • (d) Pracejus, H.; Mätje, H. Zusammenhänge Zwischen dem Räumlichen Bau Einiger Alkaloidartiger Katalysatoren und Ihren Stereospezifischen Wirkungen bei Asymmetrischen Estersynthesen. J. Prakt. Chem. 1964, 24, 195-205.
    • (1964) J. Prakt. Chem. , vol.24 , pp. 195-205
    • Pracejus, H.1    Mätje, H.2
  • 31
    • 0002172748 scopus 로고
    • Asymmetric reactions. IV. Asymmetric, catalytic activity of poly(2-quinuclidinylmethyl acrylate)
    • (e) For polymer-bound variants of the Pracejus catalyst, see: Yamashita, T.; Yasueda, H.; Nakamura, N. Asymmetric Reactions. IV. Asymmetric, Catalytic Activity of Poly(2-quinuclidinylmethyl Acrylate). Bull. Chem. Soc. Jpn. 1979, 52, 2165-2166.
    • (1979) Bull. Chem. Soc. Jpn. , vol.52 , pp. 2165-2166
    • Yamashita, T.1    Yasueda, H.2    Nakamura, N.3
  • 32
    • 0032508967 scopus 로고    scopus 로고
    • Enantioselective construction of quaternary stereocenters: Rearrangements of O-acylated azlactones catalyzed by a planar-chiral derivative of 4-(Pyrrolidino)pyridine
    • Ruble, J. C.; Fu, G. C. Enantioselective Construction of Quaternary Stereocenters: Rearrangements of O-Acylated Azlactones Catalyzed by a Planar-Chiral Derivative of 4-(Pyrrolidino)pyridine. J. Am. Chem. Soc. 1998, 120, 11532-11533.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 11532-11533
    • Ruble, J.C.1    Fu, G.C.2
  • 33
    • 0032473509 scopus 로고    scopus 로고
    • The catalytic enantioselective construction of molecules with quaternary carbon stereocenters
    • For a recent review of asymmetric synthesis of quaternary stereocenters, see: Corey, E. J.; Guzman-Perez, A. The Catalytic Enantioselective Construction of Molecules with Quaternary Carbon Stereocenters. Angew. Chem., Int. Ed. Engl. 1998, 37, 388-401. See also: Fuji, K. Asymmetric Creation of Quaternary Carbon Centers. Chem. Rev. 1993, 93, 2037-2066.
    • (1998) Angew. Chem., Int. Ed. Engl. , vol.37 , pp. 388-401
    • Corey, E.J.1    Guzman-Perez, A.2
  • 34
    • 0001521888 scopus 로고
    • Asymmetric creation of quaternary carbon centers
    • For a recent review of asymmetric synthesis of quaternary stereocenters, see: Corey, E. J.; Guzman-Perez, A. The Catalytic Enantioselective Construction of Molecules with Quaternary Carbon Stereocenters. Angew. Chem., Int. Ed. Engl. 1998, 37, 388-401. See also: Fuji, K. Asymmetric Creation of Quaternary Carbon Centers. Chem. Rev. 1993, 93, 2037-2066.
    • (1993) Chem. Rev. , vol.93 , pp. 2037-2066
    • Fuji, K.1
  • 35
    • 0030955088 scopus 로고    scopus 로고
    • New strategies to α-alkylated α-amino acids
    • and references therein
    • For a brief overview of the synthesis and the significance of α-alkylated α-amino acids, see: Wirth, T. New Strategies to α-Alkylated α-Amino Acids. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227 and references therein.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 225-227
    • Wirth, T.1
  • 36
    • 0028133330 scopus 로고
    • Efficient syntheses of the four enantiomers and diastereomers of α-methylthreonine and both enantiomers of α-methylserine
    • For a discussion of the synthesis and the significance of α-methylserine, see: Moon, S.-H.; Ohfune, Y. Efficient Syntheses of the Four Enantiomers and Diastereomers of α-Methylthreonine and Both Enantiomers of α-Methylserine. J. Am. Chem. Soc. 1994, 116, 7405-7406.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 7405-7406
    • Moon, S.-H.1    Ohfune, Y.2
  • 38
    • 0001647560 scopus 로고    scopus 로고
    • Kinetic resolution of aryl alkyl carbinols catalyzed by a planar-chiral derivative of DMAP: A new benchmark for non-enzymatic acylation
    • (b) Ruble, J. C.; Tweddell, J.; Fu, G. C. Kinetic Resolution of Aryl Alkyl Carbinols Catalyzed by a Planar-Chiral Derivative of DMAP: A New Benchmark for Non-Enzymatic Acylation. J. Org. Chem. 1998, 63, 2794-2795.
    • (1998) J. Org. Chem. , vol.63 , pp. 2794-2795
    • Ruble, J.C.1    Tweddell, J.2    Fu, G.C.3
  • 39
    • 0033516290 scopus 로고    scopus 로고
    • Non-enzymatic kinetic resolution of propargylic alcohols by a planar-chiral DMAP derivative; crystallographic characterization of the acylated catalyst
    • (c) Tao, B.; Ruble, J. C.; Hoic, D. A.; Fu, G. C. Non-Enzymatic Kinetic Resolution of Propargylic Alcohols by a Planar-Chiral DMAP Derivative; Crystallographic Characterization of the Acylated Catalyst. J. Am. Chem. Soc. 1999, 121, 5091-5092.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 5091-5092
    • Tao, B.1    Ruble, J.C.2    Hoic, D.A.3    Fu, G.C.4
  • 40
    • 85050296727 scopus 로고
    • Kinetic resolution
    • For a review of kinetic resolution, see: Kagan, H. B.; Fiaud, J. C. Kinetic Resolution. Top. Stereochem. 1988, 18, 249-330.
    • (1988) Top. Stereochem. , vol.18 , pp. 249-330
    • Kagan, H.B.1    Fiaud, J.C.2
  • 41
    • 0001526323 scopus 로고    scopus 로고
    • Enantioselective acylations catalyzed by chiral phosphines
    • (a) Vedejs, E.; Daugulis, O.; Diver, S. T. Enantioselective Acylations Catalyzed by Chiral Phosphines. J. Org. Chem. 1996, 61, 430-431.
    • (1996) J. Org. Chem. , vol.61 , pp. 430-431
    • Vedejs, E.1    Daugulis, O.2    Diver, S.T.3
  • 42
    • 0033597606 scopus 로고    scopus 로고
    • 2-Aryl-4,4,8-trimethyl-2-phosphabicyclo-[3.3.0]octanes: Reactive chiral phosphine catalysts for enantioselective acylation
    • (b) Vedejs, E.; Daugulis, O. 2-Aryl-4,4,8-trimethyl-2-phosphabicyclo-[3.3.0]octanes: Reactive Chiral Phosphine Catalysts for Enantioselective Acylation. J. Am. Chem. Soc. 1999, 121, 5813-5814.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 5813-5814
    • Vedejs, E.1    Daugulis, O.2
  • 44
    • 0033246941 scopus 로고    scopus 로고
    • Catalytic asymmetric acylation of racemic secondary alcohols with benzoyl chloride in the presence of a chiral diamine
    • (b) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Catalytic Asymmetric Acylation of Racemic Secondary Alcohols with Benzoyl Chloride in the Presence of a Chiral Diamine. Chem. Lett. 1999, 265-266.
    • (1999) Chem. Lett. , pp. 265-266
    • Sano, T.1    Imai, K.2    Ohashi, K.3    Oriyama, T.4
  • 45
    • 0030961223 scopus 로고    scopus 로고
    • Nonenzymic kinetic resolution of racemic alcohols through an "induced fit" process
    • Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. Nonenzymic Kinetic Resolution of Racemic Alcohols through an "Induced Fit" Process. J. Am. Chem. Soc. 1997, 119, 3169-3170.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 3169-3170
    • Kawabata, T.1    Nagato, M.2    Takasu, K.3    Fuji, K.4
  • 46
    • 0032564916 scopus 로고    scopus 로고
    • Kinetic resolution of alcohols catalyzed by tripeptides containing the N-alkylimidazole substructure
    • (a) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. Kinetic Resolution of Alcohols Catalyzed by Tripeptides Containing the N-Alkylimidazole Substructure. J. Am. Chem. Soc. 1998, 110, 1629-1630.
    • (1998) J. Am. Chem. Soc. , vol.110 , pp. 1629-1630
    • Miller, S.J.1    Copeland, G.T.2    Papaioannou, N.3    Horstmann, T.E.4    Ruel, E.M.5
  • 47
    • 0000089981 scopus 로고    scopus 로고
    • Minimal acylase-like peptides. Conformational control of absolute stereospecificity
    • (b) Copeland, G. T.; Jarvo, E. R.; Miller, S. J. Minimal Acylase-Like Peptides. Conformational Control of Absolute Stereospecificity. J. Org. Chem. 1998, 63, 6784-6785.
    • (1998) J. Org. Chem. , vol.63 , pp. 6784-6785
    • Copeland, G.T.1    Jarvo, E.R.2    Miller, S.J.3
  • 49
    • 0029782396 scopus 로고    scopus 로고
    • Planar-chiral ferrocenes: Synthetic methods and applications
    • (b) Togni, A. Planar-chiral Ferrocenes: Synthetic Methods and Applications. Angew. Chem., Int. Ed. Engl. 1996, 35, 1475-1477.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 1475-1477
    • Togni, A.1
  • 50
    • 0000706952 scopus 로고    scopus 로고
    • Comparing chiral ferrocenyl and ruthenocenyl ligands: How subtle structural changes influence their performance in asymmetric catalysis
    • 5 group has been reported: Abbenhuis, H. C. L.; Burckhardt, U.; Gramlich, V.; Martelletti, A.; Spencer, J.; Steiner, I.; Togni, A. Comparing Chiral Ferrocenyl and Ruthenocenyl Ligands: How Subtle Structural Changes Influence Their Performance in Asymmetric Catalysis. Organometallics 1996, 15, 1614-1621.
    • (1996) Organometallics , vol.15 , pp. 1614-1621
    • Abbenhuis, H.C.L.1    Burckhardt, U.2    Gramlich, V.3    Martelletti, A.4    Spencer, J.5    Steiner, I.6    Togni, A.7
  • 51
    • 0033603365 scopus 로고    scopus 로고
    • Preparation of 2,8-dihydroxy-5,6,-11,12-tetrahydro-5,11-epoxydibenzo[a,e]cyclooctene, an analog of Kagan's ether
    • Harmata, M.; Kahraman, M. Preparation of 2,8-Dihydroxy-5,6,-11,12-tetrahydro-5,11-epoxydibenzo[a,e]cyclooctene, An Analog of Kagan's Ether. J. Org. Chem. 1999, 64, 4949-4952.
    • (1999) J. Org. Chem. , vol.64 , pp. 4949-4952
    • Harmata, M.1    Kahraman, M.2
  • 52
    • 0343584282 scopus 로고    scopus 로고
    • Progress and problems in stereocontrolled synthesis
    • New Orleans, LA, Aug 22-26, 1999; American Chemical Society: Washington, DC, ORGN 1
    • Stork, G. Progress and Problems in Stereocontrolled Synthesis. Abstracts of Papers, 218th National Meeting of the American Chemical Society, New Orleans, LA, Aug 22-26, 1999; American Chemical Society: Washington, DC, 1999: ORGN 1.
    • (1999) Abstracts of Papers, 218th National Meeting of the American Chemical Society
    • Stork, G.1
  • 53
    • 0343148667 scopus 로고    scopus 로고
    • note
    • Catalyst 7 can also kinetically resolve certain propargylic alcohols: ref 22c.
  • 54
    • 0342714171 scopus 로고    scopus 로고
    • note
    • 2) indicate that this rotamer is also the only detectable rotamer in solution.
  • 55
    • 0342279148 scopus 로고    scopus 로고
    • note
    • For catalyst 4, which is the Cp* analogue of catalyst 7, the corresponding angle is 2°.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.