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Volumn 128, Issue 12, 2006, Pages 3928-3930

Dual-function cinchona alkaloid catalysis: Catalytic asymmetric tandem conjugate addition-protonation for the direct creation of nonadjacent stereocenters

Author keywords

[No Author keywords available]

Indexed keywords

CINCHONA ALKALOID; MANZACIDIN A; UNCLASSIFIED DRUG;

EID: 33645455231     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja060312n     Document Type: Article
Times cited : (297)

References (43)
  • 10
    • 0037145988 scopus 로고    scopus 로고
    • For asymmetric synthesis of 1,5-chiral diols, see: (a) Flamme, E. M.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 13644-13645.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 13644-13645
    • Flamme, E.M.1    Roush, W.R.2
  • 11
    • 0035862685 scopus 로고    scopus 로고
    • For construction of 1,3-tertiary-quaternary stereocenters with chiral anxiliary-directed tandem conjugate addition-protonation, see: (b) Keller, L.; Camara, C.; Pinheiro, A.; Dumas, F.; d'Angelo, J. Tetrahedron Lett. 2001, 42, 381-383.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 381-383
    • Keller, L.1    Camara, C.2    Pinheiro, A.3    Dumas, F.4    D'Angelo, J.5
  • 15
    • 0037032211 scopus 로고    scopus 로고
    • For asymmetric total syntheses of manzacidins, see: (a) Wehn, P. M.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 12950-12951.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 12950-12951
    • Wehn, P.M.1    Du Bois, J.2
  • 21
    • 30444443444 scopus 로고    scopus 로고
    • For a review of catalytic tandem asymmetric reactions triggered by conjugate addition, see: (a) Guo, H.; Ma, J. Angew. Chem., Int. Ed. 2006, 45, 354-366.
    • (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 354-366
    • Guo, H.1    Ma, J.2
  • 28
    • 14744278476 scopus 로고    scopus 로고
    • For examples of catalytic asymmetric tandem conjugate addition-protonation for the creation of two adjacent stereocenters, see: (h) Sibi, M. P.; Petrovic, G.; Zimmerman, J. J. Am. Chem. Soc. 2005, 127, 2390-2391.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 2390-2391
    • Sibi, M.P.1    Petrovic, G.2    Zimmerman, J.3
  • 34
    • 33645457461 scopus 로고    scopus 로고
    • note
    • See Supporting Information for the preparation of QD-1d.
  • 36
    • 33645451236 scopus 로고    scopus 로고
    • note
    • As described in ref 3a, Wehn and Du Bois also reported a 10-step asymmetric total synthesis of manzacidin A in which the tertiary amine is generated by a stereospecific intramolecular C-H bond amination of the corresponding methine. The required chiral methine precursor was produced via a catalytic asymmetric hydrogenation in moderate stereoselectivity.
  • 37
    • 33645461562 scopus 로고    scopus 로고
    • note
    • 99% isolated yield was obtained after a reaction time of 8 days.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.