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Volumn 129, Issue 35, 2007, Pages 10886-10894

Organocatalytic enantioselective cascade michael-alkylation reactions: Synthesis of chiral cyclopropanes and investigation of unexpected organocatalyzed stereoselective ring opening of cyclopropanes

Author keywords

[No Author keywords available]

Indexed keywords

BROMOMALONATES; CASCADE PROCESS; LEWIS ACID; MICHAEL-ALKYLATION REACTIONS; MOLECULAR ARCHITECTURES;

EID: 34848814187     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja073262a     Document Type: Article
Times cited : (321)

References (137)
  • 19
    • 0000100584 scopus 로고    scopus 로고
    • For reviews, see: a
    • For reviews, see: (a) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
    • (1998) Chem. Rev , vol.98 , pp. 911
    • Doyle, M.P.1    Forbes, D.C.2
  • 47
    • 0029563701 scopus 로고
    • For selected examples, see: a
    • For selected examples, see: (a) Charette, A. B.; Côté, B. J. Am. Chem. Soc. 1995, 117, 12721.
    • (1995) J. Am. Chem. Soc , vol.117 , pp. 12721
    • Charette, A.B.1    Côté, B.2
  • 76
    • 0000348702 scopus 로고    scopus 로고
    • The utilization of stabilized carbanions for asymmetric cyclopropanations using chiral precursors has been described; for selected examples, see: (a) McClure, D. E, Arison, B. H, Baldwin, J. J. J. Am. Chem. Soc. 1979, 101, 3666
    • The utilization of stabilized carbanions for asymmetric cyclopropanations using chiral precursors has been described; for selected examples, see: (a) McClure, D. E.; Arison, B. H.; Baldwin, J. J. J. Am. Chem. Soc. 1979, 101, 3666.
  • 85
    • 0033612173 scopus 로고    scopus 로고
    • To the best of our knowledge, prior to our initial investigation, only a single study was described by Arai and co-workers using chiral phase-transfer catalyst for cyclopropanation from α,β-ketones but with modest enantioselectivity: Arai, S.; Nakayama, K.; Ishida, T.; Shioiri, T. Tetrahedron Lett. 1999, 40, 4215.
    • To the best of our knowledge, prior to our initial investigation, only a single study was described by Arai and co-workers using chiral phase-transfer catalyst for cyclopropanation from α,β-ketones but with modest enantioselectivity: Arai, S.; Nakayama, K.; Ishida, T.; Shioiri, T. Tetrahedron Lett. 1999, 40, 4215.
  • 86
    • 33751339683 scopus 로고    scopus 로고
    • During our investigation, Hansen and co-workers reported an organocatalyzed asymmetric cyclopropanation reaction of α,β- unsaturated ketones with bromonitromethane but with modest enantioselectivities and yields: Hansen, H. M.; Longbottom, D. A.; Ley, S. V. Chem. Commun. 2006, 4838
    • During our investigation, Hansen and co-workers reported an organocatalyzed asymmetric cyclopropanation reaction of α,β- unsaturated ketones with bromonitromethane but with modest enantioselectivities and yields: Hansen, H. M.; Longbottom, D. A.; Ley, S. V. Chem. Commun. 2006, 4838
  • 87
    • 33749008198 scopus 로고    scopus 로고
    • and McCooey and co-workers described an organocatalyzed asymmetric cyclopropanation reaction of nitro-olefins with chloromalonate but with modest enantioselectivities and yields using H-bonding mediated catalysis: McCooey, S. H, McCabe, T, Connon, S. J. J. Org. Chem. 2006, 71, 7494. However, the utilization of α,β-unsaturated aldehydes reactions halostabilized carbanions for cyclopropanations have not yet reported
    • and McCooey and co-workers described an organocatalyzed asymmetric cyclopropanation reaction of nitro-olefins with chloromalonate but with modest enantioselectivities and yields using H-bonding mediated catalysis: McCooey, S. H.; McCabe, T.; Connon, S. J. J. Org. Chem. 2006, 71, 7494. However, the utilization of α,β-unsaturated aldehydes reactions halostabilized carbanions for cyclopropanations have not yet reported.
  • 88
    • 35948977080 scopus 로고    scopus 로고
    • The use of chiral auxiliaries for α-alkylation reactions, see reviews: (a) Evans, D. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; 3, Chapter 1, p 1.
    • The use of chiral auxiliaries for α-alkylation reactions, see reviews: (a) Evans, D. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; Vol. 3, Chapter 1, p 1.
  • 92
    • 0345825852 scopus 로고    scopus 로고
    • To date, only a single study of an amine-catalyzed intramolecular α-alkylation of aldehydes has been reported by List, and Vognola: Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450.
    • To date, only a single study of an amine-catalyzed intramolecular α-alkylation of aldehydes has been reported by List, and Vognola: Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450.
  • 93
    • 0003544583 scopus 로고    scopus 로고
    • For reviews, see: a, Ojima, I, Ed, Wiley-VCH: New York
    • For reviews, see: (a) O'Donnel, M. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000.
    • (2000) Catalytic Asymmetric Synthesis
    • O'Donnel, M.1
  • 100
    • 35949004156 scopus 로고    scopus 로고
    • Special Issue on Asymmetric Organocatalysis: Acc. Chem. Res. 2004, 37, 487.
    • (c) Special Issue on Asymmetric Organocatalysis: Acc. Chem. Res. 2004, 37, 487.
  • 104
  • 105
    • 0037034309 scopus 로고    scopus 로고
    • Recent selected examples of organocatalytic domino reactions, see: a
    • Recent selected examples of organocatalytic domino reactions, see: (a) Dudding, T.; Hafez, A. M.; Taggi, A. E.; Wagerle, T. R.; Lectka, T. Org. Lett. 2002, 4, 387.
    • (2002) Org. Lett , vol.4 , pp. 387
    • Dudding, T.1    Hafez, A.M.2    Taggi, A.E.3    Wagerle, T.R.4    Lectka, T.5
  • 123
    • 33747594792 scopus 로고    scopus 로고
    • Recently, we have developed organocatalytic cascade Michael-aldol/Michael processes, see: (a) Wang, W.; Li, H.; Wang, J.; Zu, L. J. Am. Chem. Soc. 2006, 128, 10354.
    • Recently, we have developed organocatalytic cascade Michael-aldol/Michael processes, see: (a) Wang, W.; Li, H.; Wang, J.; Zu, L. J. Am. Chem. Soc. 2006, 128, 10354.
  • 129
    • 34447533890 scopus 로고    scopus 로고
    • During, the submission of the manuscript, Córdova, and co-workers reported a similar organocatalytic enantioselective cyclopropanation: Rios, R.; Sundén, H.; Vesely, J.; Zhao, G.-L.; Dziedzic, P.; Córdova, A. Adv. Synth. Catal. 2007, 349, 1028.
    • During, the submission of the manuscript, Córdova, and co-workers reported a similar organocatalytic enantioselective cyclopropanation: Rios, R.; Sundén, H.; Vesely, J.; Zhao, G.-L.; Dziedzic, P.; Córdova, A. Adv. Synth. Catal. 2007, 349, 1028.
  • 130
    • 33845505476 scopus 로고    scopus 로고
    • For a review of diaryl prolinol ethers catalysis, see: a
    • For a review of diaryl prolinol ethers catalysis, see: (a) 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
  • 136
    • 35948935410 scopus 로고    scopus 로고
    • The X-ray crystal structure of compound 4a is also available from CCDC-631930. These data can be obtained free of charge via www.ccdc.cam.ac.uk.
    • The X-ray crystal structure of compound 4a is also available from CCDC-631930. These data can be obtained free of charge via www.ccdc.cam.ac.uk.
  • 137
    • 35948938283 scopus 로고    scopus 로고
    • The X-ray crystal structure of compound 5k is also available from CCDC-640204. These data can be obtained free of charge via www.ccdc.cam.ac.uk.
    • The X-ray crystal structure of compound 5k is also available from CCDC-640204. These data can be obtained free of charge via www.ccdc.cam.ac.uk.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.