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Volumn , Issue 17, 2006, Pages 3887-3897

Conformationally biased selective alkylation of trans-cyclohexane-1,2- bis(sulfonamide) assisted by solvent-tuned protecting groups: Applications to the synthesis of a large optically active polyazamacrocycle

Author keywords

Alkylation; Azamacrocycles; Conformation analysis; Protecting groups; Sulfonamides

Indexed keywords


EID: 33748545279     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600234     Document Type: Article
Times cited : (7)

References (60)
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    • 27844563112 scopus 로고    scopus 로고
    • and references cited therein
    • a) N. Kurt, S. Cavagnero, J. Am. Chem. Soc. 2005, 127, 15690-15691 and references cited therein;
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 15690-15691
    • Kurt, N.1    Cavagnero, S.2
  • 10
  • 37
  • 45
    • 0042379938 scopus 로고    scopus 로고
    • For applications of unsymmetrically substituted ligands, see: a) C. Gennari, U. Piarulli, Chem. Rev. 2003, 103, 3071-3100.
    • (2003) Chem. Rev. , vol.103 , pp. 3071-3100
    • Gennari, C.1    Piarulli, U.2
  • 52
    • 33748569211 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum shows a complicated pattern due to the presence of a mixture of conformations in solution.
  • 56
    • 1542554559 scopus 로고
    • One referee suggested that for the interpretation of our results, the Curtin-Hammett principle should be kept in mind, which states that usually it is not the stabilities of the conformers that determine the products, but rather their individual reaction rates. Thus, products are often formed entirely from less stable conformers. However, we tried to explain our experimental results by proposing a reasonable model, and considering the molecular mechanics analysis, our model reflects the trends observed experimentally. For a review on the Curtin-Hammett principle applied to conformation and reactivity, see: J. I. Seeman, Chem. Rev. 1983, 83, 83-134.
    • (1983) Chem. Rev. , vol.83 , pp. 83-134
    • Seeman, J.I.1
  • 60
    • 0842282173 scopus 로고    scopus 로고
    • Wavefunction Inc., Irvine, CA
    • Spartan 04, Wavefunction Inc., Irvine, CA.
    • Spartan 04


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.