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Volumn 130, Issue 27, 2008, Pages 8642-8650

Scope and mechanism for Lewis acid-catalyzed cycloadditions of aldehydes and donor-acceptor cyclopropanes: Evidence for a stereospecific intimate ion pair pathway

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; MECHANISMS; ORGANIC COMPOUNDS;

EID: 46949091089     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8015928     Document Type: Article
Times cited : (329)

References (71)
  • 3
    • 0037884930 scopus 로고    scopus 로고
    • D-A cyclopropane reviews: (a) Reissig, H.-U.; Zimmer, R Chem. Rev. 2003, 103, 1151-1196.
    • D-A cyclopropane reviews: (a) Reissig, H.-U.; Zimmer, R Chem. Rev. 2003, 103, 1151-1196.
  • 19
    • 33749507354 scopus 로고    scopus 로고
    • A related reaction was subsequently published: (b) Gupta, A.; Yadav, V. K Tetrahedron Lett. 2006, 47, 8043-8047.
    • A related reaction was subsequently published: (b) Gupta, A.; Yadav, V. K Tetrahedron Lett. 2006, 47, 8043-8047.
  • 49
    • 0020446324 scopus 로고    scopus 로고
    • This resolution has also been achieved with brucine: Quinkert, G, Schwartz, U, Stark, H, Weber, W-D, Adam, F, Baier, H, Frank, G, Dürner, G. Lieb. Ann. Chem. 1982, 1999-2040
    • This resolution has also been achieved with brucine: Quinkert, G.; Schwartz, U.; Stark, H.; Weber, W-D.; Adam, F.; Baier, H.; Frank, G.; Dürner, G. Lieb. Ann. Chem. 1982, 1999-2040.
  • 68
    • 46949102912 scopus 로고    scopus 로고
    • A transition structure with the oxygen on the flap of the envelope and the C2′ and C5′ substituents in the equatorial positions would provide the same product. See ref 11a
    • A transition structure with the oxygen on the flap of the envelope and the C2′ and C5′ substituents in the equatorial positions would provide the same product. See ref 11a.
  • 69
    • 46949101481 scopus 로고    scopus 로고
    • The numbering scheme changes from the cyclopropane starting material going to the tetrahydrofuran product. The prime (′) denotes an atom in the product
    • The numbering scheme changes from the cyclopropane starting material going to the tetrahydrofuran product. The prime (′) denotes an atom in the product.
  • 70
    • 33845185675 scopus 로고    scopus 로고
    • A reviewer suggested that our results may still be interpreted as an SN2 mechanism. We believe that the high site selectivity in the cycloaddition of compound 16 provides the best evidence against the SN2 mechanism. Because the SN1/SN2 continuum contains reactions proceeding via intimately associated ion pairs, the most complete description consistent with the IUPAC nomenclature for such reactions would be DN*ANint. For excellent reviews of substitution mechanisms, see: (a) Guthrie, R. D, Jencks, W. P. Acc. Chem. Res. 1989, 22, 343-349
    • Nint. For excellent reviews of substitution mechanisms, see: (a) Guthrie, R. D.; Jencks, W. P. Acc. Chem. Res. 1989, 22, 343-349.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.