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Volumn 50, Issue 48, 2011, Pages 11470-11473

Palladium-catalyzed decarboxylative intramolecular aziridination from 4h-isoxazol-5-ones leading to 1-azabicyclo[3.1.0]hex-2-enes

Author keywords

4H isoxazol 5 ones; cyclization; decarboxylation; homogeneous catalysis; palladium

Indexed keywords

4H-ISOXAZOL-5-ONES; AZIRIDINATION; AZIRIDINES; DECARBOXYLATION; DIBENZYLIDENEACETONE; HIGH YIELD; HOMOGENEOUS CATALYSIS; RING OPENING;

EID: 81755183026     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201105153     Document Type: Article
Times cited : (94)

References (42)
  • 17
    • 0034804183 scopus 로고    scopus 로고
    • Nitrene complexes of low-valent palladium or homologous elements (nickel and platinum) are rare. Well-defined zerovalent nickel/nitrene complexes have been reported by Hillhouse and Mindiola, see:, D. J. Mindiola, G. L. Hillhouse, J. Am. Chem. Soc. 2001, 123, 4623.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 4623
    • Mindiola, D.J.1    Hillhouse, G.L.2
  • 38
    • 78650350285 scopus 로고    scopus 로고
    • Recently, a rhodium(III)-catalyzed reaction of oxime esters with alkynes to give quinoline derivatives was reported by Chiba and co-workers. 4H-Isoxazol-5-ones are used in place of the oxime esters, and the decarboxylative cyclization products were obtained, see:, P. C. Too, Y. F. Wang, S. Chiba, Org. Lett. 2010, 12, 5688.
    • (2010) Org. Lett. , vol.12 , pp. 5688
    • Too, P.C.1    Wang, Y.F.2    Chiba, S.3
  • 39
    • 33845554565 scopus 로고
    • Izumi and Alper reported a palladium-catalyzed reaction of an allyl-substitued 2H-azirine to give pyrroles and pyridines (, T. Izumi, H. Alper, Organometallics 1982, 1, 322). They also proposed a vinylnitrene intermediate. Although we employed methallyl-substituted 2H-azirine 11 a as a substrate for the palladium-catalyzed intramolecular aziridination reaction, the yield of bicyclic aziridine 2 a was only 17 % [Eq.(5)].
    • (1982) Organometallics , vol.1 , pp. 322
    • Izumi, T.1    Alper, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.