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Volumn 45, Issue 36, 2006, Pages 6024-6028

Enantioselective catalytic intramolecular cyclopropanation using modified cinchona alkaloid organocatalysts

Author keywords

Asymmetric synthesis; Cinchona alkaloids; Cyclopropanation; Intramolecular reactions; Organocatalysis

Indexed keywords

ASYMMETRIC SYNTHESIS; CINCHONA ALKALOIDS; CYCLOPROPANATION; INTRAMOLECULAR REACTIONS; ORGANOCATALYSIS;

EID: 33748765777     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200602129     Document Type: Article
Times cited : (189)

References (39)
  • 5
    • 29844434876 scopus 로고    scopus 로고
    • For catalytic asymmetric intermolecular cyclopropanation reactions, see: a) B. Moreau, A. B. Charette, J. Am. Chem. Soc. 2005, 127, 18 014;
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 18014
    • Moreau, B.1    Charette, A.B.2
  • 20
    • 0000100584 scopus 로고    scopus 로고
    • c) it is also possible to form [n.1.0]-bicyclic motifs through the intermolecular cyclopropanation of cyclic alkenes; for examples, see: M. P. Doyle, D. C. Forbes, Chem. Rev. 1998, 98, 911.
    • (1998) Chem. Rev. , vol.98 , pp. 911
    • Doyle, M.P.1    Forbes, D.C.2
  • 25
    • 33748765403 scopus 로고    scopus 로고
    • note
    • a) Based on LC-mass-spectrometric analysis of the mixture; b) quinoline A, when treated with 1 a and NaBr in MeCN at 80°C, leads to an intractable mixture of products and consumes all the starting material; quinoline B does not react with 1 a under the same conditions, thus both materials are returned untouched; no cyclopropanantion was observed in these reactions.
  • 28
    • 33748764532 scopus 로고    scopus 로고
    • note
    • We also tested catalysts containing C2′-Ph (83 % yield, 96 % ee), iPr (59% yield, 98% ee), and tBu (46% yield, 93% ee), but the Me-MQ/ Me-MQD catalysts gave the best results.
  • 29
    • 33748809670 scopus 로고    scopus 로고
    • See the Supporting Information for details
    • See the Supporting Information for details.
  • 34
    • 0012083781 scopus 로고    scopus 로고
    • For a related example of intramolecular [5+2] cycloadditions, see: a) B. M. Trost, H. C. Shen, Angew. Chem. 2001, 113, 2375-2378;
    • (2001) Angew. Chem. , vol.113 , pp. 2375-2378
    • Trost, B.M.1    Shen, H.C.2
  • 35
    • 0035907913 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 2313-2316;
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 2313-2316
  • 39
    • 33748783211 scopus 로고    scopus 로고
    • note
    • The chloroketone precursors are made through an alkene cross metathesis reaction using the Grubbs second generation catalyst.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.