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Volumn 12, Issue 4, 2010, Pages 864-866

Palladium-catalyzed three-component [3 + 2] cycloaddition of propargyl trifluoroacetates, ethylidene malononitriles, and allyltributylstannane

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EID: 76849090868     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol9029275     Document Type: Article
Times cited : (6)

References (26)
  • 1
    • 33745402207 scopus 로고
    • For recent reviews, see: (a) scnore, N. E. Chem. Rev. 1988, 88, 1081.
    • (1988) Chem. Rev. , vol.88 , pp. 1081
    • Scnore, N.E.1
  • 7
    • 34547510627 scopus 로고    scopus 로고
    • For selected reviews, see: (a) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180.
    • (2007) Chem. Rev. , vol.107 , pp. 3180
    • Hashmi, A.S.K.1
  • 9
  • 18
    • 0029929193 scopus 로고    scopus 로고
    • However, 5a is not formed in the present reaction conditions without propargyl compounds.
    • 3): produces bis-π-allylpalladium complex; see: Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641. However, 5a is not formed in the present reaction conditions without propargyl compounds.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 6641
    • Nakamura, H.1    Iwama, H.2    Yamamoto, Y.3
  • 19
    • 76849097836 scopus 로고    scopus 로고
    • The reaction of other activated alkenes, such as 2-cyano-3-phenylacrylic acid methyl ester or 3-cycanochromone, gave the corresponding cyclopentene products in 20-30% yields under standard conditions.
    • The reaction of other activated alkenes, such as 2-cyano-3-phenylacrylic acid methyl ester or 3-cycanochromone, gave the corresponding cyclopentene products in 20-30% yields under standard conditions.
  • 20
    • 76849110253 scopus 로고    scopus 로고
    • An alternative reaction mechanism is a [4 + 2] cycloaddition between Pd-carbene and alkene to form, a six-membered cyclic palladium species. Subsequent reductive elimination gives the [3 + 2] cycloaddition product. However, this pathway is less reasonable for the regioselective fromation. of the corresponding cyclopentene product.
    • An alternative reaction mechanism is a [4 + 2] cycloaddition between Pd-carbene and alkene to form, a six-membered cyclic palladium species. Subsequent reductive elimination gives the [3 + 2] cycloaddition product. However, this pathway is less reasonable for the regioselective fromation. of the corresponding cyclopentene product.
  • 21
    • 16844384363 scopus 로고    scopus 로고
    • For selected examples for the formation of multisubstituted cyclopentene, see: (a) Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2005, 127, 4763-4776.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 4763-4776
    • Trost, B.M.1    Rudd, M.T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.