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Volumn 128, Issue 42, 2006, Pages 13686-13687

Highly enantioselective construction of a chiral spirocyclic structure by the [2 + 2 + 2] cycloaddition of diynes and exo-methylene cyclic compounds

Author keywords

[No Author keywords available]

Indexed keywords

ALICYCLIC HYDROCARBON; ALKENE; CARBENE; CARBENOID; SPIROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

EID: 33750357709     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja064257u     Document Type: Article
Times cited : (79)

References (23)
  • 9
    • 0034680568 scopus 로고    scopus 로고
    • An enantioselective ene-type reaction of enynes also proceeds via the metallacyclopentene with an asymmetric carbon atom: Cao, P.; Zhang, X. Angew. Chem., Int. Ed. 2000, 39, 4104.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 4104
    • Cao, P.1    Zhang, X.2
  • 10
    • 33748481111 scopus 로고    scopus 로고
    • We recently reported an enantioselective intramolecular [2 + 2 + 2] cycloaddition of 1,4-diene-yne, in which a chirality at the fused carbon atom was generated also in the metallacyclopentene intermediate: Shibata, T.; Tahara, Y. J. Am. Chem. Soc. 2006, 128, 11766.
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 11766
    • Shibata, T.1    Tahara, Y.2
  • 11
    • 4544286694 scopus 로고    scopus 로고
    • Three groups, including us, independently reported an enantioselective [2 + 2 + 2] cycloaddition of a diyne and alkyne for the generation of axial chirality; however, the chirality would be generated in the metallacyclopentadiene intermediate due to the ortho-substituted aryl groups on the diyne termini: (a) Gutnov, A.; Heller, B.; Fischer, C.; Drexler, H.-J.; Spannenberg, A.; Sundermann, B.; Sundermann, C. Angew. Chem., Int. Ed. 2004, 43, 3795.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 3795
    • Gutnov, A.1    Heller, B.2    Fischer, C.3    Drexler, H.-J.4    Spannenberg, A.5    Sundermann, B.6    Sundermann, C.7
  • 19
    • 33750286087 scopus 로고    scopus 로고
    • note
    • In the previous examples using a transition metal catalyst other than Rh catalyst, at least more than 10 equiv of alkene was used (ref 7).
  • 20
    • 0005515344 scopus 로고
    • Other approaches of transition-metal-catalyzed enantioselective synthesis of chiral spirocyclic compounds: (a) Ashimori, A.; Overman, L. K. J. Org. Chem. 1992, 57, 4571.
    • (1992) J. Org. Chem. , vol.57 , pp. 4571
    • Ashimori, A.1    Overman, L.K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.