메뉴 건너뛰기




Volumn , Issue 14, 2007, Pages 2065-2092

Organocatalytic enantioselective Michael and hetero-Michael reactions

Author keywords

Asymmetric catalysis; Asymmetric synthesis; Michael additions; Organocatalysis

Indexed keywords

ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; MICHAEL ADDITIONS; ORGANOCATALYSIS;

EID: 34547198987     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-983747     Document Type: Review
Times cited : (631)

References (299)
  • 1
    • 15244343428 scopus 로고    scopus 로고
    • General reviews: (a) Seayad, J.; List, B. Org. Biomol. Chem. 2005, 3, 719.
    • General reviews: (a) Seayad, J.; List, B. Org. Biomol. Chem. 2005, 3, 719.
  • 6
    • 34250613134 scopus 로고    scopus 로고
    • During the preparation of this manuscript, two reviews appeared covering this subject: (a) Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 1701.
    • During the preparation of this manuscript, two reviews appeared covering this subject: (a) Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 1701.
  • 8
    • 32844457119 scopus 로고    scopus 로고
    • For some reviews on asymmetric aminocatalysis, see: a
    • For some reviews on asymmetric aminocatalysis, see: (a) List, B. Chem. Commun. 2006, 819.
    • (2006) Chem. Commun , pp. 819
    • List, B.1
  • 10
  • 11
    • 0036089366 scopus 로고    scopus 로고
    • For a general review on asymmetric conjugate additions to nitroalkenes, see
    • (a) For a general review on asymmetric conjugate additions to nitroalkenes, see: Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1877.
    • (2002) Eur. J. Org. Chem , pp. 1877
    • Berner, O.M.1    Tedeschi, L.2    Enders, D.3
  • 12
    • 34547463692 scopus 로고    scopus 로고
    • For a review focused on amine-catalyzed reactions see:, in press; DOI: 10.1039/b701216k
    • (b) For a review focused on amine-catalyzed reactions see: Sulzer-Mosse, S.; Alexakis, A. Chem. Commun. 2007, in press; DOI: 10.1039/b701216k.
    • (2007) Chem. Commun
    • Sulzer-Mosse, S.1    Alexakis, A.2
  • 13
    • 34547196689 scopus 로고    scopus 로고
    • Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F. III Synthesis 2004, 1509.
    • (a) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F. III Synthesis 2004, 1509.
  • 17
    • 33847114330 scopus 로고    scopus 로고
    • For a computational study explaining the role of this catalyst in the reaction, see
    • (b) For a computational study explaining the role of this catalyst in the reaction, see: Arnó, M.; Zaragozá, R. J.; Domingo, L. R. Tetrahedron: Asymmetry 2007, 18, 157.
    • (2007) Tetrahedron: Asymmetry , vol.18 , pp. 157
    • Arnó, M.1    Zaragozá, R.J.2    Domingo, L.R.3
  • 24
    • 0142091323 scopus 로고    scopus 로고
    • For the use of a proline-valine dipeptide, see
    • (c) For the use of a proline-valine dipeptide, see: Martin, H. J.; List, B. Synlett 2003, 1901.
    • (2003) Synlett , pp. 1901
    • Martin, H.J.1    List, B.2
  • 28
    • 0035891780 scopus 로고    scopus 로고
    • Betancort, J. M.; Barbas, C. F. III Org. Lett. 2001, 3, 3737.
    • Betancort, J. M.; Barbas, C. F. III Org. Lett. 2001, 3, 3737.
  • 29
    • 4043184288 scopus 로고    scopus 로고
    • Mase, N.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F. III Org. Lett. 2004, 6, 2527.
    • Mase, N.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F. III Org. Lett. 2004, 6, 2527.
  • 31
    • 33745542958 scopus 로고    scopus 로고
    • For a related 3,3′-bimorpholine catalyst used in this reaction, see
    • (b) For a related 3,3′-bimorpholine catalyst used in this reaction, see: Mosse, S.; Laars, M.; Kriis, K.; Kanger, T.; Alexakis, A. Org. Lett. 2006, 8, 2559.
    • (2006) Org. Lett , vol.8 , pp. 2559
    • Mosse, S.1    Laars, M.2    Kriis, K.3    Kanger, T.4    Alexakis, A.5
  • 34
    • 33845505476 scopus 로고    scopus 로고
    • For a review on the use of diarylprolinol silyl ethers as organocatalysts, see
    • For a review on the use of diarylprolinol silyl ethers as organocatalysts, see: Palomo, C.; Mielgo, A. Angew. Chem. Int. Ed. 2006, 45, 7876.
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 7876
    • Palomo, C.1    Mielgo, A.2
  • 44
    • 33845648990 scopus 로고    scopus 로고
    • Albertshofer, K.; Thayumanavan, R.; Utsumi, N.; Tanaka, F.; Barbas, C. F. III Tetrahedron Lett. 2007, 48, 693.
    • Albertshofer, K.; Thayumanavan, R.; Utsumi, N.; Tanaka, F.; Barbas, C. F. III Tetrahedron Lett. 2007, 48, 693.
  • 48
    • 33646142092 scopus 로고    scopus 로고
    • Mase, N.; Watanabe, K.; Yoda, H.; Takabe, K.; Tanaka, F.; Barbas, C. F. III J. Am. Chem. Soc. 2006, 128, 4966.
    • (a) Mase, N.; Watanabe, K.; Yoda, H.; Takabe, K.; Tanaka, F.; Barbas, C. F. III J. Am. Chem. Soc. 2006, 128, 4966.
  • 49
    • 33947605163 scopus 로고    scopus 로고
    • For another recent example of a Michael reaction in water, see
    • (b) For another recent example of a Michael reaction in water, see: Singh, V.; Singh, V. K. Org. Lett. 2007, 9, 1117.
    • (2007) Org. Lett , vol.9 , pp. 1117
    • Singh, V.1    Singh, V.K.2
  • 54
    • 33750091660 scopus 로고    scopus 로고
    • For another related example, see
    • (c) For another related example, see: Xu, D.; Luo, S.; Yue, H.; Wang, L.; Xu, Z. Synlett 2006, 2569.
    • (2006) Synlett , pp. 2569
    • Xu, D.1    Luo, S.2    Yue, H.3    Wang, L.4    Xu, Z.5
  • 61
    • 34248158115 scopus 로고    scopus 로고
    • For a related work using a proline-derived aniline as catalyst, see
    • (b) For a related work using a proline-derived aniline as catalyst, see: Kikuchi, M.; Inagaki, T.; Nishiyama, H. Synlett 2007, 1075.
    • (2007) Synlett , pp. 1075
    • Kikuchi, M.1    Inagaki, T.2    Nishiyama, H.3
  • 70
    • 33847051264 scopus 로고    scopus 로고
    • For other following organocatalytic syntheses of warfarin, see: b
    • For other following organocatalytic syntheses of warfarin, see: (b) Xie, J.-S.; Yue, L.; Chen, W.; Du, W.; Zhu, J.; Deng, J.-G.; Chen, Y.-C. Org. Lett. 2007, 9, 413.
    • (2007) Org. Lett , vol.9 , pp. 413
    • Xie, J.-S.1    Yue, L.2    Chen, W.3    Du, W.4    Zhu, J.5    Deng, J.-G.6    Chen, Y.-C.7
  • 78
    • 9644295662 scopus 로고    scopus 로고
    • For a related peptide-mediated Michael reaction of nitroalkanes to cycloalkenones, see
    • (c) For a related peptide-mediated Michael reaction of nitroalkanes to cycloalkenones, see: Tsogoeva, S. B.; Jagtap, S. B. Synlett 2004, 2624.
    • (2004) Synlett , pp. 2624
    • Tsogoeva, S.B.1    Jagtap, S.B.2
  • 83
    • 17844394399 scopus 로고    scopus 로고
    • For the use of these conditions in reaction of acyclic silyl enol ethers, see
    • (b) For the use of these conditions in reaction of acyclic silyl enol ethers, see: Wang, W.; Li, H.; Wang, J. Org. Lett. 2005, 7, 1637.
    • (2005) Org. Lett , vol.7 , pp. 1637
    • Wang, W.1    Li, H.2    Wang, J.3
  • 87
    • 0034596452 scopus 로고    scopus 로고
    • Bui, T.; Barbas, C. F. III Tetrahedron Lett. 2000, 41, 6951.
    • Bui, T.; Barbas, C. F. III Tetrahedron Lett. 2000, 41, 6951.
  • 90
    • 27644444355 scopus 로고    scopus 로고
    • For a related work, see
    • (c) For a related work, see: Gryko, D. Tetrahedron: Asymmetry 2005, 16, 1377.
    • (2005) Tetrahedron: Asymmetry , vol.16 , pp. 1377
    • Gryko, D.1
  • 98
    • 33846500851 scopus 로고    scopus 로고
    • For a proline-catalyzed formal [3+3]-cycloaddition reaction between 5-methyl-3,4-dihydro-2H-pyrrole and cyclopenatenone, see: Movassaghi, M.; Chen, B. Angew. Chem. Int. Ed. 2007, 46, 565.
    • (c) For a proline-catalyzed formal [3+3]-cycloaddition reaction between 5-methyl-3,4-dihydro-2H-pyrrole and cyclopenatenone, see: Movassaghi, M.; Chen, B. Angew. Chem. Int. Ed. 2007, 46, 565.
  • 107
    • 27144522622 scopus 로고    scopus 로고
    • For a related thiourea catalysts incorporating a binaphthylamine backbone, see
    • (c) For a related thiourea catalysts incorporating a binaphthylamine backbone, see: Wang, J.; Li, H.; Duan, W.; Zu, L.; Wang, W. Org. Lett. 2005, 7, 4713.
    • (2005) Org. Lett , vol.7 , pp. 4713
    • Wang, J.1    Li, H.2    Duan, W.3    Zu, L.4    Wang, W.5
  • 149
    • 33750965601 scopus 로고    scopus 로고
    • For a recent example using methylidenemalononitriles as acceptors, see
    • (c) For a recent example using methylidenemalononitriles as acceptors, see: Kojima, S.; Suzuki, M.; Watanabe, A.; Ohkata, K. Tetrahedron Lett. 2006, 47, 9061.
    • (2006) Tetrahedron Lett , vol.47 , pp. 9061
    • Kojima, S.1    Suzuki, M.2    Watanabe, A.3    Ohkata, K.4
  • 150
    • 0033612173 scopus 로고    scopus 로고
    • For an example using 2-bromocycloalkenones as electrophiles, see
    • (d) For an example using 2-bromocycloalkenones as electrophiles, see: Arai, S.; Nakayama, K.; Ishida, T.; Shioiri, T. Tetrahedron Lett. 1999, 40, 4215.
    • (1999) Tetrahedron Lett , vol.40 , pp. 4215
    • Arai, S.1    Nakayama, K.2    Ishida, T.3    Shioiri, T.4
  • 160
    • 33749008198 scopus 로고    scopus 로고
    • For a similar reaction involving cyclopropane formation, see: b
    • For a similar reaction involving cyclopropane formation, see: (b) McCooey, S. H.; McCabe, T.; Connon, S. J. J. Org. Chem. 2006, 71, 7494.
    • (2006) J. Org. Chem , vol.71 , pp. 7494
    • McCooey, S.H.1    McCabe, T.2    Connon, S.J.3
  • 161
    • 33749520452 scopus 로고    scopus 로고
    • For further progresses expanding the scope of this reaction using catalyst 37a, see (c) Wang, J.; Li, H.; Zu, L.; Jiang, W.; Xie, H.; Duan, W.; Wang, W. J. Am. Chem. Soc. 2006, 128, 12652.
    • For further progresses expanding the scope of this reaction using catalyst 37a, see (c) Wang, J.; Li, H.; Zu, L.; Jiang, W.; Xie, H.; Duan, W.; Wang, W. J. Am. Chem. Soc. 2006, 128, 12652.
  • 180
    • 0037164617 scopus 로고    scopus 로고
    • For the use of other tartrate-derived catalysts, see
    • (c) For the use of other tartrate-derived catalysts, see: Arai, S.; Tsuji, R.; Nishida, A. Tetrahedron Lett. 2002, 43, 9535.
    • (2002) Tetrahedron Lett , vol.43 , pp. 9535
    • Arai, S.1    Tsuji, R.2    Nishida, A.3
  • 184
    • 0035801884 scopus 로고    scopus 로고
    • For an example of Michael reaction of malonates and chalcones, see
    • (d) For an example of Michael reaction of malonates and chalcones, see: Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299.
    • (2001) Tetrahedron Lett , vol.42 , pp. 6299
    • Kim, D.Y.1    Huh, S.C.2    Kim, S.M.3
  • 185
    • 0000867232 scopus 로고
    • For an example of Michael reaction of indanones and methyl vinyl ketone, see
    • (e) For an example of Michael reaction of indanones and methyl vinyl ketone, see: Conn, R. S. E.; Lovell, A. V.; Karady, S.; Weinstock, L. M. J. Org. Chem. 1986, 51, 4710.
    • (1986) J. Org. Chem , vol.51 , pp. 4710
    • Conn, R.S.E.1    Lovell, A.V.2    Karady, S.3    Weinstock, L.M.4
  • 196
    • 4143049107 scopus 로고    scopus 로고
    • For revision, see: a
    • For revision, see: (a) O'Donell, M. J. Acc. Chem. Res. 2004, 37, 506.
    • (2004) Acc. Chem. Res , vol.37 , pp. 506
    • O'Donell, M.J.1
  • 212
    • 27544485685 scopus 로고    scopus 로고
    • For a tandem enantioselective organocatalytic Friedel-Crafts alkylation-α-chlorination, see
    • (c) For a tandem enantioselective organocatalytic Friedel-Crafts alkylation-α-chlorination, see: Huang, Y.; Walji, A. M.; Larsen, C. H.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 15051.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 15051
    • Huang, Y.1    Walji, A.M.2    Larsen, C.H.3    MacMillan, D.W.C.4
  • 217
    • 34147174295 scopus 로고    scopus 로고
    • For a conjugate Friedel-Crafts alkylation of indoles with enones catalyzed by a cinchona alkaloid, see
    • (d) For a conjugate Friedel-Crafts alkylation of indoles with enones catalyzed by a cinchona alkaloid, see: Bartoli, G.; Bosco, M.; Carlone, A.; Pesciaioli, F.; Sambri, L.; Melchiorre, P. Org. Lett. 2007, 9, 1403.
    • (2007) Org. Lett , vol.9 , pp. 1403
    • Bartoli, G.1    Bosco, M.2    Carlone, A.3    Pesciaioli, F.4    Sambri, L.5    Melchiorre, P.6
  • 219
    • 33845463690 scopus 로고    scopus 로고
    • For an example of a chiral camphorsulfonic acid catalyzed conjugate Friedel-Crafts alkylation of indoles with enones, see: Zhou, W, Xu, L.-W, Li, L, Yang, L, Xia, C.-G, Chem. 2006, 5225
    • (b) For an example of a chiral camphorsulfonic acid catalyzed conjugate Friedel-Crafts alkylation of indoles with enones, see: Zhou, W.; Xu, L.-W.; Li, L.; Yang, L.; Xia, C.-G. Eur. J. Org. Chem. 2006, 5225.
  • 247
    • 0001013917 scopus 로고    scopus 로고
    • Mukaiyama has employed a simple chiral amino alcohol that mimicks the structure of cinchone alkaloids: Mukaiyama, T. Tetrahedron 1981, 37, 4111
    • (e) Mukaiyama has employed a simple chiral amino alcohol that mimicks the structure of cinchone alkaloids: Mukaiyama, T. Tetrahedron 1981, 37, 4111.
  • 253
    • 4143141139 scopus 로고    scopus 로고
    • For a review on peptide-based organocatalysts, see
    • For a review on peptide-based organocatalysts, see: Miller, S. J. Acc. Chem. Res. 2004, 37, 601.
    • (2004) Acc. Chem. Res , vol.37 , pp. 601
    • Miller, S.J.1
  • 257
    • 33847029577 scopus 로고    scopus 로고
    • For a later report using the same nucleophile and catalyst 8a, see: Vesely, J.; Ibrahem, I.; Rios, R.; Zhao, G.-L.; Xu, Y.; Cordova, A. Tetrahedron Lett. 2007, 48, 2193.
    • (b) For a later report using the same nucleophile and catalyst 8a, see: Vesely, J.; Ibrahem, I.; Rios, R.; Zhao, G.-L.; Xu, Y.; Cordova, A. Tetrahedron Lett. 2007, 48, 2193.
  • 258
    • 34248634839 scopus 로고    scopus 로고
    • For an example of amine-catalyzed conjugate addition of hydrazoic acid to nitroalkenes, see
    • (c) For an example of amine-catalyzed conjugate addition of hydrazoic acid to nitroalkenes, see: Nielsen, M.; Zhuang, W.; Jorgensen, K. A. Tetrahedron 2007, 63, 5849.
    • (2007) Tetrahedron , vol.63 , pp. 5849
    • Nielsen, M.1    Zhuang, W.2    Jorgensen, K.A.3
  • 275
    • 33644606047 scopus 로고    scopus 로고
    • Catalyst 11c: (a) Lattanzi, A
    • Catalyst 11c: (a) Lattanzi, A. Adv. Synth. Catal. 2006, 348, 339.
    • (2006) Adv. Synth. Catal , vol.348 , pp. 339
  • 276
    • 18744407280 scopus 로고    scopus 로고
    • Catalyst 8d: (b) Marigo, M.; Franzén, J.; Poulsen, T. B.; Zhuang, W.; Jørgensen, K. A. J. Am. Chem. Soc. 2005,s 127, 6964.
    • Catalyst 8d: (b) Marigo, M.; Franzén, J.; Poulsen, T. B.; Zhuang, W.; Jørgensen, K. A. J. Am. Chem. Soc. 2005,s 127, 6964.
  • 277
    • 28544436605 scopus 로고    scopus 로고
    • Catalyst 8a: (c) Sundén, H.; Ibrahem, I.; Córdova, A. Tetrahedron Lett. 2006, 47, 99.
    • Catalyst 8a: (c) Sundén, H.; Ibrahem, I.; Córdova, A. Tetrahedron Lett. 2006, 47, 99.
  • 279
    • 33846069767 scopus 로고    scopus 로고
    • Catalyst 52: (e) Li, Y.; Liu, X.; Yang, Y.; Zhao, G. J. Org. Chem. 2007, 72, 288.
    • Catalyst 52: (e) Li, Y.; Liu, X.; Yang, Y.; Zhao, G. J. Org. Chem. 2007, 72, 288.
  • 280
    • 33750445955 scopus 로고    scopus 로고
    • Catalyst ent-17c: (f) Lee, S.; MacMillan, D. W. C. Tetrahedron 2006, 62, 11413.
    • Catalyst ent-17c: (f) Lee, S.; MacMillan, D. W. C. Tetrahedron 2006, 62, 11413.
  • 287
    • 34547182502 scopus 로고    scopus 로고
    • For another very recently appeared quinine-catalyzed addition of diphenyl phosphite to nitroalkenes, see: Wang, J, Heikkinen, L. D, Li, H, Zu, L, Jiang, W, Xie, H, Wang, W. Adv. Synth. Catal. 2007, 349, 1052
    • (c) For another very recently appeared quinine-catalyzed addition of diphenyl phosphite to nitroalkenes, see: Wang, J.; Heikkinen, L. D.; Li, H.; Zu, L.; Jiang, W.; Xie, H.; Wang, W. Adv. Synth. Catal. 2007, 349, 1052.
  • 295
    • 3242812738 scopus 로고    scopus 로고
    • For the application of a modified catalyst 55 in the same reaction generating a quaternary stereocenter, see: Kerr, M. S.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 8876.
    • (c) For the application of a modified catalyst 55 in the same reaction generating a quaternary stereocenter, see: Kerr, M. S.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 8876.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.