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Volumn 43, Issue 9, 2004, Pages 1126-1129

Oxonitriles: Multicomponent Grignard addition-alkylations

Author keywords

Alkylation; Grignard reagents; Michael addition; Multicomponent reactions; Oxonitriles

Indexed keywords

ACIDS; CARBONYLATION; CHELATION; CONTROLLABILITY; SYNTHESIS (CHEMICAL);

EID: 4544304795     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352920     Document Type: Article
Times cited : (24)

References (35)
  • 8
    • 0001200413 scopus 로고    scopus 로고
    • b) A. Dömling, I. Ugi, Angew. Chem. 2000, 112, 3300; Angew. Chem. Int. Ed. 2000, 39, 3168;
    • (2000) Angew. Chem. , vol.112 , pp. 3300
    • Dömling, A.1    Ugi, I.2
  • 9
    • 0001134412 scopus 로고    scopus 로고
    • b) A. Dömling, I. Ugi, Angew. Chem. 2000, 112, 3300; Angew. Chem. Int. Ed. 2000, 39, 3168;
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3168
  • 17
    • 4544251179 scopus 로고
    • (Ed.: L. A. Paquette), Wiley, Chichester
    • 3-3,5-dimethylpyrazole[11a] rather than pyridine,[11b] afforded oxonitriles 5b and 5c in 65% and 25% yield, respectively. a) J. N. Johnson, Encyclopedia of Reagents for Organic Synthesis, Vol. 2 (Ed.: L. A. Paquette), Wiley, Chichester, 1995, pp. 1275-1277.
    • (1995) Encyclopedia of Reagents for Organic Synthesis, Vol. 2 , vol.2 , pp. 1275-1277
    • Johnson, J.N.1
  • 19
    • 4544256551 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis of the crude reaction mixture failed to identify any of the independently prepared diastereomeric nitrile.
  • 20
    • 0000232576 scopus 로고    scopus 로고
    • Methylation of 3b corresponds to a retentive alkylation of the chiral C-magnesiated nitrile, as consistently observed in the inter- and intramolecular alkylations (Table 1). The retentive alkylations of 3b contrast with invertive acylations of a closely related magnesiated nitrile[8] implying an unusual electrophile-dependent stereoselectivity analogous to that observed with selected chiral organolithium reagents.[a] Interception of 3b with a range of electrophiles is being pursued to determine if the alkylation stereoselectivity of this magnesiated nitrile is indeed electrophile dependent. a) A. Basu, S. Thayumanavan Angew. Chem. 2002, 114, 740; Angew. Chem. Int. Ed. 2002, 41, 717.
    • (2002) Angew. Chem. , vol.114 , pp. 740
    • Basu, A.1    Thayumanavan, S.2
  • 21
    • 85080848774 scopus 로고    scopus 로고
    • Methylation of 3b corresponds to a retentive alkylation of the chiral C-magnesiated nitrile, as consistently observed in the inter- and intramolecular alkylations (Table 1). The retentive alkylations of 3b contrast with invertive acylations of a closely related magnesiated nitrile[8] implying an unusual electrophile-dependent stereoselectivity analogous to that observed with selected chiral organolithium reagents.[a] Interception of 3b with a range of electrophiles is being pursued to determine if the alkylation stereoselectivity of this magnesiated nitrile is indeed electrophile dependent. a) A. Basu, S. Thayumanavan Angew. Chem. 2002, 114, 740; Angew. Chem. Int. Ed. 2002, 41, 717.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 717
  • 22
    • 4544309313 scopus 로고    scopus 로고
    • note
    • X-ray crystallography of 4b and 4c confirmed the stereochemical assignment. CCDC-218678 (4b) and CCDC-218679 (4c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam. ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
  • 29
    • 4544350009 scopus 로고    scopus 로고
    • note
    • b) Commercially available from Lancaster.
  • 30
    • 4544288601 scopus 로고    scopus 로고
    • note
    • Cyclization affords a 9:1 ratio of cis:trans abietanes in favor of 9.
  • 32
    • 4544275622 scopus 로고    scopus 로고
    • note
    • b) A 13% yield of the carbocyclic ester is formed from a carbocationic cyclization from the corresponding alkene.[18a]
  • 33
    • 0000559891 scopus 로고
    • epi-Abietic: acid 10 is used as a biological marker for diterpenoids[21a] in geochemical sediments and has been previously synthesized.[21b,c] a) B. R. T. Simoneit, Geochim. Cosmochim. Acta 1977, 41, 463;
    • (1977) Geochim. Cosmochim. Acta , vol.41 , pp. 463
    • Simoneit, B.R.T.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.