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Volumn 12, Issue 5-6, 2000, Pages 318-324

First synthesis and resolution of a planar-chiral tetrahydroindolyl complex of iron: Electronic tuning of reactivity and enantioselective nucleophilic catalysis

Author keywords

Acylation; Azaferrocene; Indolyl; Ketene

Indexed keywords

FERROCENE; INDOLEACETIC ACID;

EID: 0034040342     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(2000)12:5/6<318::AID-CHIR4>3.0.CO;2-9     Document Type: Article
Times cited : (24)

References (29)
  • 1
    • 0004221225 scopus 로고
    • New York: VCH; and references therein
    • (a) Togni A, Hayashi T, editors. Ferrocenes. New York: VCH; 1995, and references therein.
    • (1995) Ferrocenes
    • Togni, A.1    Hayashi, T.2
  • 3
    • 0000114544 scopus 로고    scopus 로고
    • Chiral π-complexes of heterocycles with transition metals: A versatile new family of nucleophilic catalysts
    • Ruble JC, Fu GC. 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
  • 4
    • 0030988976 scopus 로고    scopus 로고
    • 5) group in asymmetric catalysis
    • 5) group in asymmetric catalysis. J Am Chem Soc 1997;119: 1492-1493. Ruble JC, Tweddell J, Fu GC. Kinetic resolution of aryl alkyl carbinols catalyzed by a planar-chiral derivative of DMAP: a new benchmark for nonenzymatic acylation. J Org Chem 1998;63:2794-2795. Tao B, Ruble JC, Hoic DA, Fu GC. 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.
    • (1997) J Am Chem Soc , vol.119 , pp. 1492-1493
    • Ruble, J.C.1    Latham, H.A.2    Fu, G.C.3
  • 5
    • 0001647560 scopus 로고    scopus 로고
    • Kinetic resolution of aryl alkyl carbinols catalyzed by a planar-chiral derivative of DMAP: A new benchmark for nonenzymatic acylation
    • 5) group in asymmetric catalysis. J Am Chem Soc 1997;119: 1492-1493. Ruble JC, Tweddell J, Fu GC. Kinetic resolution of aryl alkyl carbinols catalyzed by a planar-chiral derivative of DMAP: a new benchmark for nonenzymatic acylation. J Org Chem 1998;63:2794-2795. Tao B, Ruble JC, Hoic DA, Fu GC. 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.
    • (1998) J Org Chem , vol.63 , pp. 2794-2795
    • Ruble, J.C.1    Tweddell, J.2    Fu, G.C.3
  • 6
    • 0033516290 scopus 로고    scopus 로고
    • Non-enzymatic kinetic resolution of propargylic alcohols by a planar-chiral DMAP derivative; crystallographic characterization of the acylated catalyst
    • 5) group in asymmetric catalysis. J Am Chem Soc 1997;119: 1492-1493. Ruble JC, Tweddell J, Fu GC. Kinetic resolution of aryl alkyl carbinols catalyzed by a planar-chiral derivative of DMAP: a new benchmark for nonenzymatic acylation. J Org Chem 1998;63:2794-2795. Tao B, Ruble JC, Hoic DA, Fu GC. 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
  • 7
    • 0001660358 scopus 로고    scopus 로고
    • Dynamic kinetic resolutions catalyzed by a planar-chiral derivative of DMAP: Enantioselective synthesis of protected α-amino acids from racemic azlactunes
    • (b) Liang J, Ruble JC, Fu GC. Dynamic kinetic resolutions catalyzed by a planar-chiral derivative of DMAP: Enantioselective synthesis of protected α-amino acids from racemic azlactunes. J Org Chem 1998;63:3154-3155.
    • (1998) J Org Chem , vol.63 , pp. 3154-3155
    • Liang, J.1    Ruble, J.C.2    Fu, G.C.3
  • 8
    • 0032508967 scopus 로고    scopus 로고
    • Enantio-selective construction of quaternary stereocenters: Rearrangements of O-acylated azlactones catalyzed by a planar-chiral derivative of 4-(pyrrolidino)pyridine
    • (c) Ruble JC, Fu GC. Enantio-selective 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
  • 9
    • 0033599548 scopus 로고    scopus 로고
    • Enantioselective addition of alcohols to ketenes catalyzed by a planar-chiral azaferrocene: Catalytic asymmetric synthesis of arylpropionic acids
    • (d) Hodous BL, Ruble JC, Fu GC. 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
  • 10
    • 0001111641 scopus 로고    scopus 로고
    • Planar-chiral heterocycles as ligands in metal-catalyzed processes: Enantioselective addition of organozinc reagents to aldehydes
    • (a) Dosa PI, Ruble JC, Fu GC. Planar-chiral heterocycles as ligands in metal-catalyzed processes: enantioselective addition of organozinc reagents to aldehydes. J Org Chem 1997;62:444-445.
    • (1997) J Org Chem , vol.62 , pp. 444-445
    • Dosa, P.I.1    Ruble, J.C.2    Fu, G.C.3
  • 11
    • 0032494390 scopus 로고    scopus 로고
    • 2-symmetric bisazaferrocene and its application in the enantioselective Cu(I)-catalyzed cyclopropanation of olefins
    • 2-symmetric bisazaferrocene and its application in the enantioselective Cu(I)-catalyzed cyclopropanation of olefins. J Am Chem Soc 1998;120: 10270-10271.
    • (1998) J Am Chem Soc , vol.120 , pp. 10270-10271
    • Lo, M.-C.1    Fu, G.C.2
  • 12
    • 0000565505 scopus 로고    scopus 로고
    • The first application of a planar-chiral phosphorus heterocycle in asymmetric catalysis: Enantioselective hydrogenation of dehydroamino acids
    • (c) Qiao S, Fu GC. The first application of a planar-chiral phosphorus heterocycle in asymmetric catalysis: enantioselective hydrogenation of dehydroamino acids. J Org Chem 1998;63:4168-4169.
    • (1998) J Org Chem , vol.63 , pp. 4168-4169
    • Qiao, S.1    Fu, G.C.2
  • 13
    • 37049106282 scopus 로고
    • 4-Dialkylaminopyridines: Super acylation and alkylation catalysts
    • (a) For reviews of the chemistry of DMAP, see: Scriven EFV. 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
  • 14
    • 0001557720 scopus 로고
    • Aminopyridines as acylation catalysts for tertiary alcohols
    • (b) Hassner A, Krepski LR, 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
  • 15
    • 0001062066 scopus 로고
    • New synthetic-methods. 25. 4-Dialkylaminopyridines as acylation catalysts. 4. Puridine syntheses. 1. 4-Dialkylaminopyridines as highly active acylation catalysts
    • (c) Höfle G, Steglich W. Vorbrüggen H. New synthetic-methods. 25. 4-Dialkylaminopyridines as acylation catalysts. 4. Puridine syntheses. 1. 4-Dialkylaminopyridines as highly active acylation catalysts. Angew Chem, Int Ed Engl 1978;17:569-583.
    • (1978) Angew Chem, Int Ed Engl , vol.17 , pp. 569-583
    • Höfle, G.1    Steglich, W.2    Vorbrüggen, H.3
  • 16
    • 85182611423 scopus 로고
    • Aminopyrroles
    • Jones RA, editor. New York: Wiley Interscience
    • For a discussion, see: Cirrincione G, Almerico AM, Aiello E, Dattolo G. Aminopyrroles. In: Jones RA, editor. Pyrroles. New York: Wiley Interscience; 1992.
    • (1992) Pyrroles
    • Cirrincione, G.1    Almerico, A.M.2    Aiello, E.3    Dattolo, G.4
  • 17
    • 0342565964 scopus 로고
    • Derivatives of indole. CXIII. Synthesis and some properties of 3-aminoindole
    • For example, crystalline 3-aminoindole "can be stored without appreciable signs of decomposition for a long time." See: Yarosh AV, Velezheva VS, Kozik TA, Suvorov NN. Derivatives of indole. CXIII. Synthesis and some properties of 3-aminoindole. Khim Geterotsik1 Soedin 1977;481-485.
    • (1977) Khim Geterotsik1 Soedin , pp. 481-485
    • Yarosh, A.V.1    Velezheva, V.S.2    Kozik, T.A.3    Suvorov, N.N.4
  • 18
    • 0007408550 scopus 로고
    • Zur kenntnis einiger arylierter ketoketene
    • Pracejus H, Wallura G. Zur Kenntnis einiger arylierter Ketoketene J Prakt Chem 1963;19:33-36.
    • (1963) J Prakt Chem , vol.19 , pp. 33-36
    • Pracejus, H.1    Wallura, G.2
  • 20
    • 0002209617 scopus 로고
    • Acetic formic anhydride
    • Krimen LI. Acetic formic anhydride. Org Synth 1970;50:1-3.
    • (1970) Org Synth , vol.50 , pp. 1-3
    • Krimen, L.I.1
  • 22
    • 0004099973 scopus 로고
    • Metal complexes of heterocycles. II. N-pyrrolyl complexes of iron
    • 5-indolyl) FeCp may be accessible, but he has not provided details: Pauson PL, Qazi AR. Metal complexes of heterocycles. II. N-pyrrolyl complexes of iron. J Organomet Chem 1967;7:321-324.
    • (1967) J Organomet Chem , vol.7 , pp. 321-324
    • Pauson, P.L.1    Qazi, A.R.2
  • 24
    • 33947332992 scopus 로고
    • Kinetics and mechanism of substitution reactions of π-cyclopentadienyldicarbonylrhodium
    • 5 ring slippage of a cyclopentadienyl group, see: Schuster-Woldan HG, Basolo F. Kinetics and mechanism of substitution reactions of π-cyclopentadienyldicarbonylrhodium. J Am Chem Soc 1966;88:1657-1663.
    • (1966) J Am Chem Soc , vol.88 , pp. 1657-1663
    • Schuster-Woldan, H.G.1    Basolo, F.2
  • 25
    • 37049122372 scopus 로고
    • Reactions of π-indenyl complexes of transition metals. I. Kinetics and mechanisms of reactions of tricarbonyl-π-indenylmethylmolybdenum with phosphorus (III) ligands
    • 3, see: Hart-Davis AJ, Mawby RJ. Reactions of π-indenyl complexes of transition metals. I. Kinetics and mechanisms of reactions of tricarbonyl-π-indenylmethylmolybdenum with phosphorus (III) ligands. J Chem Soc (A) 1969;2403-2407. Rerek ME, Ji L-N, Basolo FJ. The indenyl ligand effect on the rate of substitution reactions of dicarbonyl(η-indenyl)rhodium and tricarbonyl(η-indenyl)manganese. Chem Soc, Chem Commun 1983;1208-1209.
    • (1969) J Chem Soc (A) , pp. 2403-2407
    • Hart-Davis, A.J.1    Mawby, R.J.2
  • 26
    • 0038281244 scopus 로고
    • The indenyl ligand effect on the rate of substitution reactions of dicarbonyl(η-indenyl)rhodium and tricarbonyl(η-indenyl)manganese
    • 3, see: Hart-Davis AJ, Mawby RJ. Reactions of π-indenyl complexes of transition metals. I. Kinetics and mechanisms of reactions of tricarbonyl-π-indenylmethylmolybdenum with phosphorus (III) ligands. J Chem Soc (A) 1969;2403-2407. Rerek ME, Ji L-N, Basolo FJ. The indenyl ligand effect on the rate of substitution reactions of dicarbonyl(η-indenyl)rhodium and tricarbonyl(η-indenyl)manganese. Chem Soc, Chem Commun 1983;1208-1209.
    • (1983) Chem Soc, Chem Commun , pp. 1208-1209
    • Rerek, M.E.1    Ji, L.-N.2    Basolo, F.J.3
  • 27
    • 11644324798 scopus 로고
    • Ring-slippage chemistry of transition metal cyclopentadienyl and indenyl complexes
    • (c) For a review of ring slippage, see: O'Connor JM, Casey CP. Ring-slippage chemistry of transition metal cyclopentadienyl and indenyl complexes. Chem Rev 1987;87:307-318.
    • (1987) Chem Rev , vol.87 , pp. 307-318
    • O'Connor, J.M.1    Casey, C.P.2
  • 28
    • 84941401510 scopus 로고
    • Di-tetrahydroindenyl-eisen
    • 2, see: Fischer EO, Seus DZ. Di-tetrahydroindenyl-eisen. Naturforsch 1954;9b:386.
    • (1954) Naturforsch , vol.9 B , pp. 386
    • Fischer, E.O.1    Seus, D.Z.2
  • 29
    • 0000308108 scopus 로고
    • For a review of kinetic resolution, see: Kagan hb, fiaud jc, kinetic resolution
    • Selectivity factor = (rate of fast-reacting enantiomer)/(rate of slow-reacting enantiomer). For a review of kinetic resolution, see: Kagan HB, Fiaud JC, Kinetic resolution. Top Stereochem 1988;18:249-330.
    • (1988) Top Stereochem , vol.18 , pp. 249-330


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