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Volumn 75, Issue 22, 2010, Pages 7901-7904

Josiphos-catalyzed asymmetric homodimerization of ketoketenes

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC SYSTEM; CHIRAL PHOSPHINE; DIASTEREO-SELECTIVITY; DIKETONES; ENOL ESTERS; HOMODIMERIZATION; RING OPENING REACTION;

EID: 78449245046     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101867m     Document Type: Article
Times cited : (50)

References (50)
  • 20
    • 78449263616 scopus 로고    scopus 로고
    • Abstracts of Papers, 236th National Meeting of the American Chemical Society, Philadelphia, PA; American Chemical Society: Washington, DC,; ORGN 531
    • Kerrigan, N. J.; Ibrahim, A. A.; Harzmann, G. D. Abstracts of Papers, 236th National Meeting of the American Chemical Society, Philadelphia, PA; American Chemical Society: Washington, DC, 2008; ORGN 531.
    • (2008)
    • Kerrigan, N.J.1    Ibrahim, A.A.2    Harzmann, G.D.3
  • 29
    • 11144311055 scopus 로고    scopus 로고
    • Lewis base-catalyzed enantioselective approaches to β-lactones from ketoketenes and aldehydes
    • Lewis base-catalyzed enantioselective approaches to β-lactones from ketoketenes and aldehydes: Wilson, J. E.; Fu, G. C. Angew. Chem., Int. Ed. 2004, 43, 6358-6360
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 6358-6360
    • Wilson, J.E.1    Fu, G.C.2
  • 35
    • 0037181062 scopus 로고    scopus 로고
    • Ferrocenylamines possessing planar chirality have been extensively used to catalyze asymmetric reactions of ketoketenes, see
    • Ferrocenylamines possessing planar chirality have been extensively used to catalyze asymmetric reactions of ketoketenes, see: Hodous, B. L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 1578-1579
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 1578-1579
    • Hodous, B.L.1    Fu, G.C.2
  • 37
    • 84904448376 scopus 로고    scopus 로고
    • Reference 9a
    • Reference 9a.
  • 38
    • 84904448377 scopus 로고    scopus 로고
    • MOP, BINAP, and various phosphepines gave low enantioselectivity (<30% ee) for the dimerization of methylphenylketene 1a
    • MOP, BINAP, and various phosphepines gave low enantioselectivity (<30% ee) for the dimerization of methylphenylketene 1a.
  • 39
    • 84904448369 scopus 로고    scopus 로고
    • Josiphos derivatives 4a - e are available from Aldrich and from Strem
    • Josiphos derivatives 4a - e are available from Aldrich and from Strem.
  • 40
    • 84904448370 scopus 로고    scopus 로고
    • Josiphos-catalyzed homodimerization of isopropylmethylketene also gave the 1,3-cyclobutanedione regioisomer, with only trace β-lactone being formed
    • Josiphos-catalyzed homodimerization of isopropylmethylketene also gave the 1,3-cyclobutanedione regioisomer, with only trace β-lactone being formed.
  • 46
    • 84904448371 scopus 로고    scopus 로고
    • The relative stereochemistry of 10b was confirmed to be syn by a comparison with the spectroscopic data presented in ref 8. The relative stereochemistry of 8a has not been determined. Both 8a and 9a were determined to be optically active (see the Supporting Information) but the ee values of 8a and 9a were not determined unambiguously by HPLC analysis. However, as no bonds at the quaternary stereocenter are cleaved in the formation of 8a or 9a, retention of chirality is assumed
    • The relative stereochemistry of 10b was confirmed to be syn by a comparison with the spectroscopic data presented in ref 8. The relative stereochemistry of 8a has not been determined. Both 8a and 9a were determined to be optically active (see the Supporting Information) but the ee values of 8a and 9a were not determined unambiguously by HPLC analysis. However, as no bonds at the quaternary stereocenter are cleaved in the formation of 8a or 9a, retention of chirality is assumed.
  • 47
    • 0037189897 scopus 로고    scopus 로고
    • For preparation of ketoketenes see
    • For preparation of ketoketenes see: Hodous, B. L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 10006-10007
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 10006-10007
    • Hodous, B.L.1    Fu, G.C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.