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Volumn 455, Issue 7211, 2008, Pages 323-332

Natural products as inspiration for the development of asymmetric catalysis

Author keywords

[No Author keywords available]

Indexed keywords

CYANTHIWIGIN F; FLUSTRAMINE B; FLUVIRUCININE A1; HARMICINE; INDACRINONE; MARCFORTINE; MARCFORTINE B; MINFIENSINE; NATURAL PRODUCT; NATURAL PRODUCTS AND THEIR SYNTHETIC DERIVATIVES; SITAGLIPTIN; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

EID: 52449100159     PISSN: 00280836     EISSN: 14764687     Source Type: Journal    
DOI: 10.1038/nature07370     Document Type: Review
Times cited : (216)

References (100)
  • 2
    • 0003445429 scopus 로고    scopus 로고
    • Jacobsen, E. N, Pfaltz, A. & Yamamoto, H, eds, Springer
    • Jacobsen, E. N., Pfaltz, A. & Yamamoto, H. (eds) Comprehensive Asymmetric Catalysis Vol. I-III (Springer, 2000).
    • (2000) Comprehensive Asymmetric Catalysis , vol.I-III
  • 3
    • 84945504205 scopus 로고    scopus 로고
    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H. (eds) Comprehensive Asymmetric Catalysis Suppl. 1 & 2 (Springer, 2004).
    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H. (eds) Comprehensive Asymmetric Catalysis Suppl. 1 & 2 (Springer, 2004).
  • 4
    • 0001852710 scopus 로고    scopus 로고
    • eds Vögtle, F, Stoddart, J. F. & Shibasaki, M, Wiley-VCH
    • Hoveyda, A. H. in Stimulating Concepts in Chemistry (eds Vögtle, F., Stoddart, J. F. & Shibasaki, M.) 145-160 (Wiley-VCH, 2000).
    • (2000) Stimulating Concepts in Chemistry , pp. 145-160
    • Hoveyda, A.H.1
  • 5
    • 1842631437 scopus 로고    scopus 로고
    • Asymmetric catalysis: An enabling science
    • Trost, B. M. Asymmetric catalysis: an enabling science. Proc. Natl Acad. Sci. USA 101, 5348-5355 (2004).
    • (2004) Proc. Natl Acad. Sci. USA , vol.101 , pp. 5348-5355
    • Trost, B.M.1
  • 6
    • 1842862775 scopus 로고    scopus 로고
    • Asymmetric catalysis in complex target synthesis
    • Taylor, M. S. & Jacobsen, E. N. Asymmetric catalysis in complex target synthesis. Proc. Natl Acad. Sci. USA 101, 5368-5373 (2004).
    • (2004) Proc. Natl Acad. Sci. USA , vol.101 , pp. 5368-5373
    • Taylor, M.S.1    Jacobsen, E.N.2
  • 7
    • 84962105974 scopus 로고
    • Synthesen in der Hydroaromatischen Reihe
    • Diels, O. & Alder, K. Synthesen in der Hydroaromatischen Reihe. Justus Liebigs Ann. Chem. 460, 98-122 (1928).
    • (1928) Justus Liebigs Ann. Chem , vol.460 , pp. 98-122
    • Diels, O.1    Alder, K.2
  • 8
    • 0009146189 scopus 로고    scopus 로고
    • Stork, G., van Tamalen, E. E., Friedman, L. J. & Burgstahler, A. W. Cantharidin. A stereospecific total synthesis. J. Am. Chem. Soc. 73, 4501 (1951).
    • Stork, G., van Tamalen, E. E., Friedman, L. J. & Burgstahler, A. W. Cantharidin. A stereospecific total synthesis. J. Am. Chem. Soc. 73, 4501 (1951).
  • 10
    • 33947480910 scopus 로고
    • Acceleration of the Diels-Alder reaction by aluminum chloride
    • Yates, P. & Eaton, P. Acceleration of the Diels-Alder reaction by aluminum chloride. J. Am. Chem. Soc. 82, 4436-4437 (1960).
    • (1960) J. Am. Chem. Soc , vol.82 , pp. 4436-4437
    • Yates, P.1    Eaton, P.2
  • 11
    • 37049112759 scopus 로고
    • Asymmetric Diels-Alder reaction catalysed by chiral alkoxyaluminium dichloride
    • Hashimoto, S.-i., Komeshima, N. & Koga, K. Asymmetric Diels-Alder reaction catalysed by chiral alkoxyaluminium dichloride. J. Chem. Soc. Chem. Commun. 437-438 (1979).
    • (1979) J. Chem. Soc. Chem. Commun , vol.437-438
    • Hashimoto, S.-I.1    Komeshima, N.2    Koga, K.3
  • 13
    • 0036263839 scopus 로고    scopus 로고
    • Catalytic enantioselective Diels-Alder reactions: Methods, mechanistic fundamentals, pathways, and applications
    • Corey, E. J. Catalytic enantioselective Diels-Alder reactions: methods, mechanistic fundamentals, pathways, and applications. Angew. Chem. Int. Edn Engl. 41, 1650-1667 (2002).
    • (2002) Angew. Chem. Int. Edn Engl , vol.41 , pp. 1650-1667
    • Corey, E.J.1
  • 16
    • 33845282438 scopus 로고
    • A stable and easily prepared catalyst for the enantioselective reduction of ketones. Applications to multistep syntheses
    • Corey, E. J., Bakshi, R. K., Shibata, S., Chen, C.-P. & Singh, V. K. A stable and easily prepared catalyst for the enantioselective reduction of ketones. Applications to multistep syntheses. J. Am. Chem. Soc. 109, 7925-7926 (1987).
    • (1987) J. Am. Chem. Soc , vol.109 , pp. 7925-7926
    • Corey, E.J.1    Bakshi, R.K.2    Shibata, S.3    Chen, C.-P.4    Singh, V.K.5
  • 17
    • 0032541271 scopus 로고    scopus 로고
    • Reduction of carbonyl compounds with chiral oxazaborolidine catalysts: A new paradigm for enantioselective catalysis and a powerful new synthetic method
    • Corey, E. J & Helal, C. J. Reduction of carbonyl compounds with chiral oxazaborolidine catalysts: a new paradigm for enantioselective catalysis and a powerful new synthetic method. Angew. Chem. Int. Edn Engl. 37, 1986-2012 (1998).
    • (1998) Angew. Chem. Int. Edn Engl , vol.37 , pp. 1986-2012
    • Corey, E.J.1    Helal, C.J.2
  • 18
    • 0037436454 scopus 로고    scopus 로고
    • Privileged chiral catalysts
    • Yoon, T. P. & Jacobsen, E. N. Privileged chiral catalysts. Science 229, 1691-1693 (2003).
    • (2003) Science , vol.229 , pp. 1691-1693
    • Yoon, T.P.1    Jacobsen, E.N.2
  • 19
    • 36849051865 scopus 로고    scopus 로고
    • Catalytic asymmetric synthesis of α-amino acids
    • Nájera, C. & Sansano, J. M. Catalytic asymmetric synthesis of α-amino acids. Chem. Rev. 107, 4584-4671 (2007).
    • (2007) Chem. Rev , vol.107 , pp. 4584-4671
    • Nájera, C.1    Sansano, J.M.2
  • 22
    • 0000305326 scopus 로고
    • Beyond nature's chiral pool: Enantioselective catalysis in industry
    • Nugent, W. A., RajanBabu, T. V. & Burk, M. J. Beyond nature's chiral pool: enantioselective catalysis in industry. Science 259, 479-483 (1993).
    • (1993) Science , vol.259 , pp. 479-483
    • Nugent, W.A.1    RajanBabu, T.V.2    Burk, M.J.3
  • 23
    • 33747054198 scopus 로고    scopus 로고
    • Asymmetric synthesis of active pharmaceutical ingredients
    • Farina, V., Reeves, J. T., Senanayake, C. H. & Song, J. J. Asymmetric synthesis of active pharmaceutical ingredients. Chem. Rev. 106, 2734-2793 (2006).
    • (2006) Chem. Rev , vol.106 , pp. 2734-2793
    • Farina, V.1    Reeves, J.T.2    Senanayake, C.H.3    Song, J.J.4
  • 25
    • 84981886574 scopus 로고
    • New type of asymmetric cyclization to optically active steroid CD partial structures
    • Eder, U., Sauer, G. & Wiechert, R. New type of asymmetric cyclization to optically active steroid CD partial structures. Angew. Chem. Int. Edn Engl. 10, 496-497 (1971).
    • (1971) Angew. Chem. Int. Edn Engl , vol.10 , pp. 496-497
    • Eder, U.1    Sauer, G.2    Wiechert, R.3
  • 26
    • 0015855293 scopus 로고
    • Stereocontrolled total synthesis of 19-nor steroids
    • Hajos, Z. G. & Parrish, D. R. Stereocontrolled total synthesis of 19-nor steroids. J. Org. Chem. 38, 3244-3249 (1973).
    • (1973) J. Org. Chem , vol.38 , pp. 3244-3249
    • Hajos, Z.G.1    Parrish, D.R.2
  • 27
    • 33847804003 scopus 로고
    • Asymmetric synthesis of bicyclic intermediates of natural product chemistry
    • Hajos, Z. G. & Parrish, D. R. Asymmetric synthesis of bicyclic intermediates of natural product chemistry. J. Org. Chem. 39, 1615-1621 (1974).
    • (1974) J. Org. Chem , vol.39 , pp. 1615-1621
    • Hajos, Z.G.1    Parrish, D.R.2
  • 28
    • 0034684178 scopus 로고    scopus 로고
    • Application of complex aldol reactions to the total synthesis of phorboxazole B
    • Evans, D. A., Fitch, D. M., Smith, T. E. & Cee, V. J. Application of complex aldol reactions to the total synthesis of phorboxazole B. J. Am. Chem. Soc. 122, 10033-10046 (2000).
    • (2000) J. Am. Chem. Soc , vol.122 , pp. 10033-10046
    • Evans, D.A.1    Fitch, D.M.2    Smith, T.E.3    Cee, V.J.4
  • 29
    • 0037016618 scopus 로고    scopus 로고
    • The aldol addition reaction: An old transformation at constant rebirth
    • Palomo, C., Oiarbide, M. & García, J. M. The aldol addition reaction: an old transformation at constant rebirth. Chem. Eur. J. 8, 37-44 (2002).
    • (2002) Chem. Eur. J , vol.8 , pp. 37-44
    • Palomo, C.1    Oiarbide, M.2    García, J.M.3
  • 30
    • 0141869057 scopus 로고    scopus 로고
    • Recent developments in the catalytic asymmetric synthesis of α- and β-amino acids
    • Ma, J.-A. Recent developments in the catalytic asymmetric synthesis of α- and β-amino acids. Angew. Chem. Int. Edn Engl. 42, 4290-4299 (2003).
    • (2003) Angew. Chem. Int. Edn Engl , vol.42 , pp. 4290-4299
    • Ma, J.-A.1
  • 33
    • 0025895518 scopus 로고
    • Enantioselective synthesis of β-amino acids based on BINAP-ruthenium(ii) catalyzed hydrogenation
    • Lubell, W. D., Kitamura, M. & Noyori, R. Enantioselective synthesis of β-amino acids based on BINAP-ruthenium(ii) catalyzed hydrogenation. Tetrahedr. Asymmetry 2, 543-554 (1991).
    • (1991) Tetrahedr. Asymmetry , vol.2 , pp. 543-554
    • Lubell, W.D.1    Kitamura, M.2    Noyori, R.3
  • 34
    • 0037708569 scopus 로고    scopus 로고
    • Chiral β-amino acid derivatives via asymmetric hydrogenation
    • Drexler, H.-J. et al. Chiral β-amino acid derivatives via asymmetric hydrogenation. Org. Process Res. Dev. 7, 355-361 (2003).
    • (2003) Org. Process Res. Dev , vol.7 , pp. 355-361
    • Drexler, H.-J.1
  • 36
    • 4043110495 scopus 로고    scopus 로고
    • Highly efficient synthesis of β-amino acid derivatives via asymmetric hydrogenation of unprotected enamines
    • This paper describes the discovery of the rhodium-catalysed enantioselective hydrogenation of β-enamino amide and ester substrates
    • Hsiao, Y. et al. Highly efficient synthesis of β-amino acid derivatives via asymmetric hydrogenation of unprotected enamines. J. Am. Chem. Soc. 126, 9918-9919 (2004). This paper describes the discovery of the rhodium-catalysed enantioselective hydrogenation of β-enamino amide and ester substrates.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 9918-9919
    • Hsiao, Y.1
  • 37
    • 38049047508 scopus 로고    scopus 로고
    • Unlocking the potential of asymmetric hydrogenation at Merck
    • Shultz, C. S. & Krska, S. W. Unlocking the potential of asymmetric hydrogenation at Merck. Acc. Chem Res. 40, 1320-1326 (2007).
    • (2007) Acc. Chem Res , vol.40 , pp. 1320-1326
    • Shultz, C.S.1    Krska, S.W.2
  • 38
    • 5644289358 scopus 로고    scopus 로고
    • Mechanistic evidence for an α-oxoketene pathway in the formation of β-ketoamides/esters via Meldrum's acid adducts
    • Xu, F. et al. Mechanistic evidence for an α-oxoketene pathway in the formation of β-ketoamides/esters via Meldrum's acid adducts. J. Am. Chem. Soc. 126, 13002-13009 (2004).
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 13002-13009
    • Xu, F.1
  • 39
    • 33746916498 scopus 로고    scopus 로고
    • Clausen, A. M. et al. Identification of ammonium chloride as an effective promoter of the asymmetric hydrogenation of β-enamine amide. Org. Process Res. Dev. 10, 723-726 (2006). This paper details efforts to scale up the enantioselective hydrogenation of a β-enamino amide towards the industrial-scale synthesis of the type 2 diabetes treatment sitagliptin (Januvia), as well as the impact of using ammonium chloride as an additive to maintain efficiency and selectivity in this process.
    • Clausen, A. M. et al. Identification of ammonium chloride as an effective promoter of the asymmetric hydrogenation of β-enamine amide. Org. Process Res. Dev. 10, 723-726 (2006). This paper details efforts to scale up the enantioselective hydrogenation of a β-enamino amide towards the industrial-scale synthesis of the type 2 diabetes treatment sitagliptin (Januvia), as well as the impact of using ammonium chloride as an additive to maintain efficiency and selectivity in this process.
  • 40
    • 1842732187 scopus 로고    scopus 로고
    • Toward efficient asymmetric hydrogenation: Architectural and functional engineering of chiral molecular catalysts
    • Noyori, R., Kitamura, M. & Ohkuma, T. Toward efficient asymmetric hydrogenation: architectural and functional engineering of chiral molecular catalysts. Proc. Natl Acad. Sci. USA 101, 5356-5362 (2004).
    • (2004) Proc. Natl Acad. Sci. USA , vol.101 , pp. 5356-5362
    • Noyori, R.1    Kitamura, M.2    Ohkuma, T.3
  • 42
    • 20544450502 scopus 로고    scopus 로고
    • de Meijere, A. & Diederich, F, eds, Vols & 2 Wiley-VCH
    • de Meijere, A. & Diederich, F. (eds) Metal-Catalyzed Cross-Coupling Reactions Vols 1 & 2 (Wiley-VCH, 2004).
    • (2004) Metal-Catalyzed Cross-Coupling Reactions , vol.1
  • 43
    • 0034249479 scopus 로고    scopus 로고
    • Transition metal-catalyzed activation of aliphatic C-X bonds in carbon-carbon bond formation
    • Luh, T.-Y., Leung, M.-K. & Wong, K.-T. Transition metal-catalyzed activation of aliphatic C-X bonds in carbon-carbon bond formation. Chem. Rev. 100, 3187-3204 (2000).
    • (2000) Chem. Rev , vol.100 , pp. 3187-3204
    • Luh, T.-Y.1    Leung, M.-K.2    Wong, K.-T.3
  • 44
    • 13444263825 scopus 로고    scopus 로고
    • Catalysts for cross-coupling reactions with non-activated alkyl halides
    • Frisch, A. C. & Beller, M. Catalysts for cross-coupling reactions with non-activated alkyl halides. Angew. Chem. Int. Edn Engl. 44, 674-688 (2005).
    • (2005) Angew. Chem. Int. Edn Engl , vol.44 , pp. 674-688
    • Frisch, A.C.1    Beller, M.2
  • 46
    • 33748447889 scopus 로고
    • Asymmetric cross-coupling reactions of sec-alkyl Grignard reagents with organic halides in the presence of a chiral phosphine-nickel complex as a catalyst
    • Kiso, Y., Tamao, K., Miyake, N., Yamamoto, K. & Kumada, M. Asymmetric cross-coupling reactions of sec-alkyl Grignard reagents with organic halides in the presence of a chiral phosphine-nickel complex as a catalyst. Tetrahedr. Lett. 15, 3-6 (1974).
    • (1974) Tetrahedr. Lett , vol.15 , pp. 3-6
    • Kiso, Y.1    Tamao, K.2    Miyake, N.3    Yamamoto, K.4    Kumada, M.5
  • 47
    • 0001717911 scopus 로고
    • Asymmetric synthesis catalyzed by chiral ferrocenylphosphine-transition metal complexes. 2. Nickel- and palladium-catalyzed asymmetric Grignard cross-coupling
    • Hayashi, T. et al. Asymmetric synthesis catalyzed by chiral ferrocenylphosphine-transition metal complexes. 2. Nickel- and palladium-catalyzed asymmetric Grignard cross-coupling. J. Am. Chem. Soc. 104, 180-186 (1982).
    • (1982) J. Am. Chem. Soc , vol.104 , pp. 180-186
    • Hayashi, T.1
  • 48
    • 16844363000 scopus 로고    scopus 로고
    • Asymmetric nickel-catalyzed Negishi cross-couplings of secondary α-bromo amides with organozinc reagents
    • Fischer, C. & Fu, G. C. Asymmetric nickel-catalyzed Negishi cross-couplings of secondary α-bromo amides with organozinc reagents. J. Am. Chem. Soc. 127, 4594-4595 (2005).
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 4594-4595
    • Fischer, C.1    Fu, G.C.2
  • 49
    • 23044496800 scopus 로고    scopus 로고
    • Catalytic enantioselective Negishi reactions of racemic secondary benzylic halides
    • Arp, F. O. & Fu, G. C. Catalytic enantioselective Negishi reactions of racemic secondary benzylic halides. J. Am. Chem. Soc. 127, 10482-10483 (2005).
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 10482-10483
    • Arp, F.O.1    Fu, G.C.2
  • 50
    • 0344861888 scopus 로고    scopus 로고
    • Cross-couplings of unactivated secondary alkyl halides: Room-temperature nickel-catalyzed Negishi reactions of alkyl bromides and iodides
    • Zhou, J. & Fu, G. C. Cross-couplings of unactivated secondary alkyl halides: room-temperature nickel-catalyzed Negishi reactions of alkyl bromides and iodides. J. Am. Chem. Soc. 125, 14726-14727 (2003).
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 14726-14727
    • Zhou, J.1    Fu, G.C.2
  • 51
    • 40949123444 scopus 로고    scopus 로고
    • Nickel-catalyzed asymmetric Negishi cross-couplings of secondary allylic chlorides with alkylzincs
    • 1
    • 1.
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 2756-2757
    • Son, S.1    Fu, G.C.2
  • 53
    • 1842851813 scopus 로고    scopus 로고
    • Catalytic asymmetric synthesis of all-carbon quaternary stereocenters
    • Douglas, C. J. & Overman, L. E. Catalytic asymmetric synthesis of all-carbon quaternary stereocenters. Proc. Natl Acad. Sci. USA 101, 5363-5367 (2004).
    • (2004) Proc. Natl Acad. Sci. USA , vol.101 , pp. 5363-5367
    • Douglas, C.J.1    Overman, L.E.2
  • 54
    • 4444264948 scopus 로고
    • Palladium-catalyzed reactions of organic halides with olefins
    • Heck, R. F. Palladium-catalyzed reactions of organic halides with olefins. Acc. Chem. Res. 12, 146-151 (1979).
    • (1979) Acc. Chem. Res , vol.12 , pp. 146-151
    • Heck, R.F.1
  • 55
    • 84942221470 scopus 로고
    • Application of intramolecular Heck reactions for forming congested quaternary carbon centers in complex molecule total synthesis
    • Overman, L. E. Application of intramolecular Heck reactions for forming congested quaternary carbon centers in complex molecule total synthesis. Pure Appl. Chem. 66, 1423-1430 (1994).
    • (1994) Pure Appl. Chem , vol.66 , pp. 1423-1430
    • Overman, L.E.1
  • 56
    • 0000438986 scopus 로고
    • Catalytic asymmetric carbon-carbon bond formation: Asymmetric synthesis of cis-decalin derivatives by palladium-catalyzed cyclization of prochiral alkenyl iodides
    • Sato, Y., Sodeoka, M. & Shibasaki, M. Catalytic asymmetric carbon-carbon bond formation: asymmetric synthesis of cis-decalin derivatives by palladium-catalyzed cyclization of prochiral alkenyl iodides. J. Org. Chem. 54, 4738-4739 (1989).
    • (1989) J. Org. Chem , vol.54 , pp. 4738-4739
    • Sato, Y.1    Sodeoka, M.2    Shibasaki, M.3
  • 57
    • 0000052196 scopus 로고
    • Palladium-catalyzed polyene cyclizations of trienyl triflates
    • Carpenter, N. E., Kucera, D. J. & Overman, L. E. Palladium-catalyzed polyene cyclizations of trienyl triflates. J. Org. Chem. 54, 5846-5848 (1989).
    • (1989) J. Org. Chem , vol.54 , pp. 5846-5848
    • Carpenter, N.E.1    Kucera, D.J.2    Overman, L.E.3
  • 58
    • 0042379984 scopus 로고    scopus 로고
    • The asymmetric intramolecular Heck reaction in natural product total synthesis
    • Dounay, A. B. & Overman, L. E. The asymmetric intramolecular Heck reaction in natural product total synthesis. Chem. Rev. 103, 2945-2963 (2003).
    • (2003) Chem. Rev , vol.103 , pp. 2945-2963
    • Dounay, A.B.1    Overman, L.E.2
  • 60
    • 22944450392 scopus 로고    scopus 로고
    • Sequential catalytic asymmetric Heck-iminium ion cyclization: Enantioselective total synthesis of the Strychnos alkaloid minfiensine
    • Dounay, A. B., Overman, L. E. & Wrobleski, A. D. Sequential catalytic asymmetric Heck-iminium ion cyclization: enantioselective total synthesis of the Strychnos alkaloid minfiensine. J. Am. Chem. Soc. 127, 10186-10187 (2005).
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 10186-10187
    • Dounay, A.B.1    Overman, L.E.2    Wrobleski, A.D.3
  • 61
    • 42149168996 scopus 로고    scopus 로고
    • Total synthesis of the Strychnos alkaloid (+)-minfiensine: Tandem enantioselective intramolecular Heck-iminium ion cyclization
    • This paper provides a full account of the use of the palladium-catalysed enantioselective Heck reaction for total synthesis of the alkaloid minfiensine
    • Dounay, A. B., Humphreys, P. G., Overman, L. E. & Wrobleski, A. D. Total synthesis of the Strychnos alkaloid (+)-minfiensine: tandem enantioselective intramolecular Heck-iminium ion cyclization. J. Am. Chem. Soc. 130, 5368-5377 (2008). This paper provides a full account of the use of the palladium-catalysed enantioselective Heck reaction for total synthesis of the alkaloid minfiensine.
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 5368-5377
    • Dounay, A.B.1    Humphreys, P.G.2    Overman, L.E.3    Wrobleski, A.D.4
  • 62
    • 35048894985 scopus 로고    scopus 로고
    • Intramolecular Heck reactions of unactivated alkyl halides
    • Kirmansjah, L. & Fu, G. C. Intramolecular Heck reactions of unactivated alkyl halides. J. Am. Chem. Soc. 129, 11340-11341 (2008).
    • (2008) J. Am. Chem. Soc , vol.129 , pp. 11340-11341
    • Kirmansjah, L.1    Fu, G.C.2
  • 64
    • 33746864043 scopus 로고    scopus 로고
    • Practical methodologies for the synthesis of indoles
    • Humphrey, G. R. & Kuethe, J. T. Practical methodologies for the synthesis of indoles. Chem. Rev. 106, 2875-2911 (2006).
    • (2006) Chem. Rev , vol.106 , pp. 2875-2911
    • Humphrey, G.R.1    Kuethe, J.T.2
  • 65
    • 0035825178 scopus 로고    scopus 로고
    • Catalytic asymmetric Friedel-Crafts alkylation of β,γ-unsaturated α-ketoesters: Enantioselective addition of aromatic C-H bonds to alkenes
    • Jensen, K. B., Thorhauge, J., Hazell, R. G. & Jørgensen, K. A. Catalytic asymmetric Friedel-Crafts alkylation of β,γ-unsaturated α-ketoesters: enantioselective addition of aromatic C-H bonds to alkenes. Angew. Chem. Int. Edn Engl. 40, 160-163 (2001).
    • (2001) Angew. Chem. Int. Edn Engl , vol.40 , pp. 160-163
    • Jensen, K.B.1    Thorhauge, J.2    Hazell, R.G.3    Jørgensen, K.A.4
  • 66
    • 0034807741 scopus 로고    scopus 로고
    • New strategies in organic catalysis: The first enantioselective organocatalytic Friedel-Crafts alkylation
    • Paras, N. A. & MacMillan, D. W. C. New strategies in organic catalysis: the first enantioselective organocatalytic Friedel-Crafts alkylation. J. Am. Chem. Soc. 123, 4370-4371 (2001).
    • (2001) J. Am. Chem. Soc , vol.123 , pp. 4370-4371
    • Paras, N.A.1    MacMillan, D.W.C.2
  • 67
    • 33745715054 scopus 로고    scopus 로고
    • Modern strategies in organic catalysis: The advent and development of iminium activation
    • Lelais, G. & MacMillan, D. W. C. Modern strategies in organic catalysis: the advent and development of iminium activation. Aldrichimica Acta 39, 79-87 (2006).
    • (2006) Aldrichimica Acta , vol.39 , pp. 79-87
    • Lelais, G.1    MacMillan, D.W.C.2
  • 69
    • 0037138701 scopus 로고    scopus 로고
    • Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis
    • Austin, J. F. & MacMillan, D. W. C. Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis. J. Am. Chem. Soc. 124, 1172-1173 (2002).
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 1172-1173
    • Austin, J.F.1    MacMillan, D.W.C.2
  • 70
    • 0011167360 scopus 로고
    • ed. Brossi, A, Academic
    • Hino, T. & Nakagawa, M. in The Alkaloids Vol. 34 (ed. Brossi, A.) 1-75 (Academic, 1988).
    • (1988) The Alkaloids , vol.34 , pp. 1-75
    • Hino, T.1    Nakagawa, M.2
  • 71
    • 0033603864 scopus 로고    scopus 로고
    • Direct stereo- and enantiocontrolled synthesis of vicinal stereogenic quaternary carbon centers. Total syntheses of meso- and (-)-chimonanthine and (+)-calycanthine
    • Overman, L. E., Paone, D. V. & Stearns, B. A. Direct stereo- and enantiocontrolled synthesis of vicinal stereogenic quaternary carbon centers. Total syntheses of meso- and (-)-chimonanthine and (+)-calycanthine. J. Am. Chem. Soc. 121, 7702-7703 (1999).
    • (1999) J. Am. Chem. Soc , vol.121 , pp. 7702-7703
    • Overman, L.E.1    Paone, D.V.2    Stearns, B.A.3
  • 72
    • 0034598476 scopus 로고    scopus 로고
    • Enantioselective construction of vicinal stereogenic quaternary stereocenters by dialkylation: Practical total syntheses of (+)- and meso-chimonanthine
    • Overman, L. E., Larrow, J. F., Stearns, B. A. & Vance, J. M. Enantioselective construction of vicinal stereogenic quaternary stereocenters by dialkylation: practical total syntheses of (+)- and meso-chimonanthine. Angew. Chem. Int. Edn Engl. 39, 213-215 (2000).
    • (2000) Angew. Chem. Int. Edn Engl , vol.39 , pp. 213-215
    • Overman, L.E.1    Larrow, J.F.2    Stearns, B.A.3    Vance, J.M.4
  • 73
    • 0033616097 scopus 로고    scopus 로고
    • Total synthesis of 5-N-acetylardeemin and amauromine: Practical routes to potential MDR reversal agents
    • Depew, K. M. et al. Total synthesis of 5-N-acetylardeemin and amauromine: Practical routes to potential MDR reversal agents. J. Am. Chem. Soc. 121, 11953-11963 (1999).
    • (1999) J. Am. Chem. Soc , vol.121 , pp. 11953-11963
    • Depew, K.M.1
  • 74
    • 1842732181 scopus 로고    scopus 로고
    • Austin, J. F., Kim, S.-G., Sinz, C. J., Xiao, W.-J. & MacMillan, D. W. C. Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition-cyclization strategy: synthesis of (-)-flustramine B. Proc. Natl Acad. Sci. USA 101, 5482-5487 (2004). This paper describes the use of imidazolidinone catalysts for enantioselective Friedel-Crafts reactions with indole nucleophiles for the synthesis of the potassium-channel blocker flustramine B.
    • Austin, J. F., Kim, S.-G., Sinz, C. J., Xiao, W.-J. & MacMillan, D. W. C. Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition-cyclization strategy: synthesis of (-)-flustramine B. Proc. Natl Acad. Sci. USA 101, 5482-5487 (2004). This paper describes the use of imidazolidinone catalysts for enantioselective Friedel-Crafts reactions with indole nucleophiles for the synthesis of the potassium-channel blocker flustramine B.
  • 75
    • 84937424396 scopus 로고
    • Über die Bildung von Isochinolin-derivaten durch Einwirkung von Methylal auf Phenyl-äthylamin, Phenyl-alanin und Tyrosin.
    • Pictet, A. & Spengler, T. Über die Bildung von Isochinolin-derivaten durch Einwirkung von Methylal auf Phenyl-äthylamin, Phenyl-alanin und Tyrosin. Ber. Dtsch. Chem. Ges. 44, 2030-2036 (1911).
    • (1911) Ber. Dtsch. Chem. Ges , vol.44 , pp. 2030-2036
    • Pictet, A.1    Spengler, T.2
  • 76
    • 4243241249 scopus 로고
    • The Pictet-Spengler condensation: A new direction for an old reaction
    • Cox, E. D. & Cook, J. M. The Pictet-Spengler condensation: a new direction for an old reaction. Chem. Rev. 95, 1797-1842 (1995).
    • (1995) Chem. Rev , vol.95 , pp. 1797-1842
    • Cox, E.D.1    Cook, J.M.2
  • 77
    • 34447290697 scopus 로고    scopus 로고
    • A new asymmetric synthesis of the natural enantiomer of the indolizidino[8,7- b]indole alkaloid (+)-harmicine
    • Allin, S. M., Gaskell, S. N., Elsegood, M. R. J. & Martin, W. P. A new asymmetric synthesis of the natural enantiomer of the indolizidino[8,7- b]indole alkaloid (+)-harmicine. Tetrahedr. Lett. 48, 5669-5671 (2007).
    • (2007) Tetrahedr. Lett , vol.48 , pp. 5669-5671
    • Allin, S.M.1    Gaskell, S.N.2    Elsegood, M.R.J.3    Martin, W.P.4
  • 78
    • 4344713238 scopus 로고    scopus 로고
    • Highly enantioselective catalytic acyl-Pictet-Spengler reactions
    • Taylor, M. S. & Jacobsen, E. N. Highly enantioselective catalytic acyl-Pictet-Spengler reactions. J. Am. Chem. Soc. 126, 10558-10559 (2004).
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 10558-10559
    • Taylor, M.S.1    Jacobsen, E.N.2
  • 79
    • 31944452587 scopus 로고    scopus 로고
    • Catalytic asymmetric Pictet-Spengler reaction
    • Seayad, J., Seayad, A. M. & List, B. Catalytic asymmetric Pictet-Spengler reaction. J. Am. Chem. Soc. 128, 1086-1087 (2006).
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 1086-1087
    • Seayad, J.1    Seayad, A.M.2    List, B.3
  • 81
    • 35948942795 scopus 로고    scopus 로고
    • Enantioselective Pictet-Spengler-type cyclizations of hydroxylactams: H-bond donor catalysis by anion binding
    • This paper describes development of the thiourea-catalysed enantioselective Pictet-Spengler-type cyclization reaction used in the synthesis of the compound harmicine, which is active against leishmaniasis
    • Raheem, I. T., Thiara, P. S., Peterson, E. A. & Jacobsen, E. N. Enantioselective Pictet-Spengler-type cyclizations of hydroxylactams: H-bond donor catalysis by anion binding. J. Am. Chem. Soc. 129, 13404-13405 (2007). This paper describes development of the thiourea-catalysed enantioselective Pictet-Spengler-type cyclization reaction used in the synthesis of the compound harmicine, which is active against leishmaniasis.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 13404-13405
    • Raheem, I.T.1    Thiara, P.S.2    Peterson, E.A.3    Jacobsen, E.N.4
  • 82
    • 44449107794 scopus 로고    scopus 로고
    • Regio- and enantioselective catalytic cyclization of pyrroles onto N-acyliminium ions
    • Raheem, I. T., Thiara, P. S. & Jacobsen, E. N. Regio- and enantioselective catalytic cyclization of pyrroles onto N-acyliminium ions. Org. Lett. 10, 1577-1580 (2008).
    • (2008) Org. Lett , vol.10 , pp. 1577-1580
    • Raheem, I.T.1    Thiara, P.S.2    Jacobsen, E.N.3
  • 83
    • 44949230317 scopus 로고    scopus 로고
    • Enantioselective thiourea-catalyzed additions to oxocarbenium ions
    • Reisman, S. E., Doyle, A. G. & Jacobsen, E. N. Enantioselective thiourea-catalyzed additions to oxocarbenium ions. J. Am. Chem. Soc. 130, 7198-7199 (2008).
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 7198-7199
    • Reisman, S.E.1    Doyle, A.G.2    Jacobsen, E.N.3
  • 84
    • 33845470711 scopus 로고
    • Efficient catalytic asymmetric alkylations. 1. Enantioselective synthesis of (+)-indacrinone via chiral phase-transfer catalysis
    • This paper describes the use of cinchoninium catalysts for enantioselective enolate alkylation towards synthesizing the diuretic indacrinone
    • Dolling, U.-H., Davis, P. & Grabowski, E. J. J. Efficient catalytic asymmetric alkylations. 1. Enantioselective synthesis of (+)-indacrinone via chiral phase-transfer catalysis. J. Am. Chem. Soc. 106, 446-447 (1984). This paper describes the use of cinchoninium catalysts for enantioselective enolate alkylation towards synthesizing the diuretic indacrinone.
    • (1984) J. Am. Chem. Soc , vol.106 , pp. 446-447
    • Dolling, U.-H.1    Davis, P.2    Grabowski, E.J.J.3
  • 85
    • 0000637655 scopus 로고
    • Efficient catalytic asymmetric alkylations. 3. A kinetic and mechanistic study of the enantioselective phase-transfer methylation of 6,7-dichloro-5-methoxy-2-phenyl-1-indanone
    • Hughes, D. L., Dolling, U.-H., Ryan, K. M., Schoenewaldt, E. F. & Grabowski, E. J. J. Efficient catalytic asymmetric alkylations. 3. A kinetic and mechanistic study of the enantioselective phase-transfer methylation of 6,7-dichloro-5-methoxy-2-phenyl-1-indanone. J. Org. Chem. 52, 4745-4752 (1987).
    • (1987) J. Org. Chem , vol.52 , pp. 4745-4752
    • Hughes, D.L.1    Dolling, U.-H.2    Ryan, K.M.3    Schoenewaldt, E.F.4    Grabowski, E.J.J.5
  • 87
    • 46349090301 scopus 로고    scopus 로고
    • The total synthesis of (-)-cyanthiwigin F by means of double catalytic enantioselective alkylation
    • This paper details the use of palladium-catalysed enantioselective enolate alkylation for the total synthesis of the marine natural product cyanthiwigin F
    • Enquist, J. A. Jr & Stoltz, B. M. The total synthesis of (-)-cyanthiwigin F by means of double catalytic enantioselective alkylation. Nature 453, 1228-1231 (2008). This paper details the use of palladium-catalysed enantioselective enolate alkylation for the total synthesis of the marine natural product cyanthiwigin F.
    • (2008) Nature , vol.453 , pp. 1228-1231
    • Enquist Jr, J.A.1    Stoltz, B.M.2
  • 88
    • 36949022498 scopus 로고    scopus 로고
    • Enantioselective Tsuji allylations
    • Mohr, J. T. & Stoltz, B. M. Enantioselective Tsuji allylations. Chem. Asian J. 2, 1476-1491 (2007).
    • (2007) Chem. Asian J , vol.2 , pp. 1476-1491
    • Mohr, J.T.1    Stoltz, B.M.2
  • 89
    • 9344253873 scopus 로고    scopus 로고
    • The enantioselective Tsuji allylation
    • Behenna, D. C. & Stoltz, B. M. The enantioselective Tsuji allylation. J. Am. Chem. Soc. 126, 15044-15045 (2004).
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 15044-15045
    • Behenna, D.C.1    Stoltz, B.M.2
  • 90
    • 27544451620 scopus 로고    scopus 로고
    • Deracemization of quaternary stereocenters by Pd-catalyzed enantioconvergenent decarboxylative allylation of racemic β-ketoesters
    • Mohr, J. T., Behenna, D. C., Harned, A. M. & Stoltz, B. M. Deracemization of quaternary stereocenters by Pd-catalyzed enantioconvergenent decarboxylative allylation of racemic β-ketoesters. Angew. Chem. Int. Edn Engl. 44, 6924-6927 (2005).
    • (2005) Angew. Chem. Int. Edn Engl , vol.44 , pp. 6924-6927
    • Mohr, J.T.1    Behenna, D.C.2    Harned, A.M.3    Stoltz, B.M.4
  • 91
    • 35648986618 scopus 로고    scopus 로고
    • Catalytic enantioselective stereoablative reactions: An unexploited approach to enantioselective catalysis
    • Mohr, J. T., Ebner, D. C. & Stoltz, B. M. Catalytic enantioselective stereoablative reactions: an unexploited approach to enantioselective catalysis. Org. Biomol. Chem. 5, 3571-3576 (2007).
    • (2007) Org. Biomol. Chem , vol.5 , pp. 3571-3576
    • Mohr, J.T.1    Ebner, D.C.2    Stoltz, B.M.3
  • 92
    • 0038614390 scopus 로고    scopus 로고
    • 3 + 2] Cycloaddition of trimethylenemethane and its synthetic equivalents
    • Yamago, S. & Nakamura, E. [3 + 2] Cycloaddition of trimethylenemethane and its synthetic equivalents. Org. React. 61, 1-217 (2002).
    • (2002) Org. React , vol.61 , pp. 1-217
    • Yamago, S.1    Nakamura, E.2
  • 93
    • 0012014342 scopus 로고
    • New conjunctive reagents. 2-Acetoxymethyl-3-allyltrimethylsilane for methylenecyclopentane annulations catalyzed by palladium(0)
    • Trost, B. M. & Chan, D. M. T. New conjunctive reagents. 2-Acetoxymethyl-3-allyltrimethylsilane for methylenecyclopentane annulations catalyzed by palladium(0). J. Am. Chem. Soc. 101, 6429-6432 (1979).
    • (1979) J. Am. Chem. Soc , vol.101 , pp. 6429-6432
    • Trost, B.M.1    Chan, D.M.T.2
  • 94
    • 0000570425 scopus 로고
    • 2-Acetoxymethyl-3-allyltrimethylsilane and palladium(0): A source of trimethylenemethane-palladium complex?
    • Trost, B. M. & Chan, D. M. T. 2-Acetoxymethyl-3-allyltrimethylsilane and palladium(0): a source of trimethylenemethane-palladium complex? J. Am. Chem. Soc. 101, 6432-6433 (1979).
    • (1979) J. Am. Chem. Soc , vol.101 , pp. 6432-6433
    • Trost, B.M.1    Chan, D.M.T.2
  • 95
    • 33947389932 scopus 로고    scopus 로고
    • Concise total synthesis of (±)-marcfortine B
    • This paper describes the synthetic route to (±)-marcfortine B
    • Trost, B. M., Cramer, N. & Bernsmann, H. Concise total synthesis of (±)-marcfortine B. J. Am. Chem. Soc. 129, 3086-3087 (2007). This paper describes the synthetic route to (±)-marcfortine B.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 3086-3087
    • Trost, B.M.1    Cramer, N.2    Bernsmann, H.3
  • 96
    • 44949154712 scopus 로고    scopus 로고
    • Enantioselective palladium-catalyzed trimethylenemethane [3 + 2] cycloadditions
    • Le Marquand, P. & Tam, W. Enantioselective palladium-catalyzed trimethylenemethane [3 + 2] cycloadditions. Angew. Chem. Int. Edn Engl. 47, 2926-2928 (2008).
    • (2008) Angew. Chem. Int. Edn Engl , vol.47 , pp. 2926-2928
    • Le Marquand, P.1    Tam, W.2
  • 97
    • 0343536779 scopus 로고
    • Asymmetric [3 + 2] cycloaddition of 2-(sulfonylmethyl)-2-propenyl carbonate catalyzed by chiral ferrocenylphosphine-palladium complexes
    • Yamamoto, A., Ito, Y. & Hayashi, T. Asymmetric [3 + 2] cycloaddition of 2-(sulfonylmethyl)-2-propenyl carbonate catalyzed by chiral ferrocenylphosphine-palladium complexes. Tetrahedr. Lett. 30, 375-378 (1989).
    • (1989) Tetrahedr. Lett , vol.30 , pp. 375-378
    • Yamamoto, A.1    Ito, Y.2    Hayashi, T.3
  • 98
    • 33750053278 scopus 로고    scopus 로고
    • Palladium-catalyzed asymmetric [3 + 2] trimethylenemethane cycloaddition reactions
    • Trost, B. M., Stambuli, J. P., Silverman, S. M. & Schwörer, W. Palladium-catalyzed asymmetric [3 + 2] trimethylenemethane cycloaddition reactions. J. Am. Chem. Soc. 128, 13328-13329 (2006).
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 13328-13329
    • Trost, B.M.1    Stambuli, J.P.2    Silverman, S.M.3    Schwörer, W.4
  • 99
    • 35348943329 scopus 로고    scopus 로고
    • Enantioselective construction of spirocyclic oxindolic cyclopentanes by palladium-catalyzed trimethylenemethane [3 + 2]-cycloaddition
    • This paper describes palladium-catalysed enantioselective TMM [3, 2] cycloaddition with oxindoles, which might provide an enantioselective route to marcfortine B
    • Trost, B. M., Cramer, N. & Silverman, S. M. Enantioselective construction of spirocyclic oxindolic cyclopentanes by palladium-catalyzed trimethylenemethane [3 + 2]-cycloaddition. J. Am. Chem. Soc. 129, 12396-12397 (2007). This paper describes palladium-catalysed enantioselective TMM [3 + 2] cycloaddition with oxindoles, which might provide an enantioselective route to marcfortine B.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 12396-12397
    • Trost, B.M.1    Cramer, N.2    Silverman, S.M.3
  • 100
    • 35348988125 scopus 로고    scopus 로고
    • Palladium-catalyzed asymmetric [3 + 2] cycloaddition of trimethylenemethane with imines
    • Trost, B. M., Silverman, S. M. & Stambuli, J. P. Palladium-catalyzed asymmetric [3 + 2] cycloaddition of trimethylenemethane with imines. J. Am. Chem. Soc. 129, 12398-12399 (2007).
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 12398-12399
    • Trost, B.M.1    Silverman, S.M.2    Stambuli, J.P.3


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