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Volumn 45, Issue 25, 2006, Pages 4172-4175

Pericyclic cascade reactions of (bicyclo[1.1.0]butylmethyl)amines

Author keywords

Bicyclobutanes; Cascade reactions pericyclic reactions; Pyrrolidines; Spirocycles

Indexed keywords

CHEMICAL ANALYSIS; PHASE TRANSITIONS;

EID: 33746301755     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200600723     Document Type: Article
Times cited : (63)

References (38)
  • 6
    • 0004258370 scopus 로고
    • (Ed.: Z. Rappoport), Wiley, New York
    • S. Hoz in The Chemistry of Cyclopropyl Group (Ed.: Z. Rappoport), Wiley, New York, 1987, pp. 1121-1192.
    • (1987) The Chemistry of Cyclopropyl Group , pp. 1121-1192
    • Hoz, S.1
  • 7
    • 0001227151 scopus 로고
    • a) Y. Gaoni, Tetrahedron 1989, 45, 2819-2840;
    • (1989) Tetrahedron , vol.45 , pp. 2819-2840
    • Gaoni, Y.1
  • 18
    • 33746280442 scopus 로고    scopus 로고
    • note
    • The remainder of the material was starting material 1 or rearranged allylcyclopropylbenzylamine.
  • 29
    • 33746271240 scopus 로고    scopus 로고
    • note
    • The structure of 5 was assigned based on the X-ray analysis of the ketoaldehyde derived from cleavage of the cyclobutene ring.
  • 30
    • 33746283266 scopus 로고    scopus 로고
    • note
    • The relative stereochemistry of 12 was assigned based on NOESY analysis.
  • 31
    • 33746300724 scopus 로고    scopus 로고
    • note
    • A steric argument was used to rationalize the selectivity of the ene versus [2+2] pathway for simple bicyclo[1.1.0]butanes (see reference [12]); prior pericyclic reactions of bicyclo[1.1.0]butanes were limited to structurally simple substrates, and no further synthetic applications were reported.
  • 32
    • 33746308295 scopus 로고    scopus 로고
    • note
    • Reaction of 3-phenylbicyclo[1.1.0]butyllithium with acetaldehyde or benzaldehyde followed by phase-transfer alkylation resulted in a low yield of the alkylated product.
  • 33
    • 0346046471 scopus 로고
    • For a demonstration of the radical nature of reactions of bicyclo[2.1.0]pentane with alkenes, see: a) P. G. Gassman, K. T. Mansfield, T. J. Murphy, J. Am. Chem. Soc. 1969, 91, 1684-1689;
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 1684-1689
    • Gassman, P.G.1    Mansfield, K.T.2    Murphy, T.J.3
  • 36
    • 0000134041 scopus 로고    scopus 로고
    • a) T. Linker, Angew. Chem. 1997, 109, 2150-2152;
    • (1997) Angew. Chem. , vol.109 , pp. 2150-2152
    • Linker, T.1
  • 38
    • 33746296104 scopus 로고    scopus 로고
    • note
    • b) alkene Z/E isomerization during N-alkylation was not responsible for the lack of stereospecificity; (Z)-cinnamyl bromide when treated with N-(3-phenylprop-2-ynyl)diphenylphosphinylamide gives an alkylated product with an intact Z double-bond configuration in 67% yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.