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Volumn 70, Issue 12, 2005, Pages 4714-4719

Highly selective reaction of α-halo-αβ-unsaturated esters with ketones or aldehydes promoted by SmI2: An efficient alternative access to Baylis-Hillman adducts

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ALDEHYDES; AROMATIC COMPOUNDS; KETONES; PHASE TRANSITIONS; REACTION KINETICS; SAMARIUM COMPOUNDS; SYNTHESIS (CHEMICAL); UNSATURATED COMPOUNDS;

EID: 20344398198     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0504969     Document Type: Article
Times cited : (12)

References (33)
  • 3
    • 4744362831 scopus 로고
    • To see reviews of the Baylis-Hillman reaction: (a) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653-4670.
    • (1988) Tetrahedron , vol.44 , pp. 4653-4670
    • Drewes, S.E.1    Roos, G.H.P.2
  • 14
    • 0000104215 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK
    • (c) Molander, G. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 1, pp 251-282.
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 251-282
    • Molander, G.A.1
  • 15
    • 0001367782 scopus 로고
    • Paquette, L. A., Ed.: John Wiley: New York
    • (d) Molander, G. A. In Organic Reactions; Paquette, L. A., Ed.: John Wiley: New York, 1994; Vol. 46, pp 211-367.
    • (1994) Organic Reactions , vol.46 , pp. 211-367
    • Molander, G.A.1
  • 20
    • 0346787791 scopus 로고    scopus 로고
    • (i) Kagan, H. B. Tetrahedron 2003, 59, 10351-10372.
    • (2003) Tetrahedron , vol.59 , pp. 10351-10372
    • Kagan, H.B.1
  • 24
    • 20344390183 scopus 로고    scopus 로고
    • note
    • Although a true inversion of configuration of the C=C double bond takes place, the nomenclature to designate the relative configuration of the starting unsaturated ketone and the Baylis-Hillman product is Z in both cases.
  • 25
    • 0000696943 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK
    • This (Z)-adducts are complementary of those obtained by organocopper 1,4-adition-aldol reactions of propargylic esters, which can produce (E)-adducts: Kozlowski, J. A. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 5, pp 169-198.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 169-198
    • Kozlowski, J.A.1
  • 27
    • 20344377072 scopus 로고    scopus 로고
    • note
    • 2-polyether complexes would display strong one-electron-transfer ability but with a reduced ability to coordinate with carbonyl oxygen, thus pinacol coupling would be reduced.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.