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Volumn 37, Issue 23, 1981, Pages 3981-3996

Chemical consequences of conformation in macrocyclic compounds. An effective approach to remote asymmetric induction1 1 This work was presented in part at the Fourteenth Sheffield Stereochemistry Symposium in Sheffield, England, on December 17, 1980.

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EID: 1542532787     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)93273-9     Document Type: Article
Times cited : (366)

References (58)
  • 1
    • 84918333311 scopus 로고    scopus 로고
    • This work was presented in part at the Fourteenth Sheffield Stereochemistry Symposium in Sheffield, England, on December 17, 1980.
  • 6
    • 0018361824 scopus 로고
    • Specific examples of macrocyclically controlled syntheses include
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 2493
    • Still1
  • 27
    • 0000010344 scopus 로고
    • Exploratory Calculations of Medium and Large Rings. Part 1. Conformational Minima of Cycloalkanes.
    • (1973) Acta Chemica Scandinavica , vol.27 , pp. 1115
    • Dale1
  • 28
    • 0012094246 scopus 로고
    • Exploratory Calculations of Medium and Large Rings. Part 3. Mono- and Bis(gem-dimethyl)cycloalkanes.
    • (1973) Acta Chemica Scandinavica , vol.27 , pp. 1149
    • Dale1
  • 29
    • 0008374834 scopus 로고
    • Exploratory Calculations of Medium and Large Rings. Part 2. Conformational Interconversions in Cycloalkanes.
    • (1973) Acta Chemica Scandinavica , vol.27 , pp. 1130
    • Dale1
  • 33
    • 3042988525 scopus 로고
    • MM2 is available from Indiana University's Quantum Chemistry Program Exchange as program Number 395.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 8127
    • Allinger1
  • 34
    • 0018361824 scopus 로고
    • For an application of peripheral stereoselection to a complex synthetic problem see
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 2493
    • Still1
  • 36
    • 84918333310 scopus 로고    scopus 로고
    • 3 and the carbinol hydrogen absorbed at 3.20 ppm as a doublet of doublets (J = 2.2 and 9.5 Hz).
  • 38
    • 84918333309 scopus 로고    scopus 로고
    • Enolate silylation and NMR examination showed at least 10:1 regioselection for the more substituted enolate.
  • 41
    • 84918333308 scopus 로고    scopus 로고
    • This lack of stereoselectivity is somewhat surprising and the reason for the poor results are not clear at this time. We have not excluded for example the possibilities of product equilibration or initial formation of a stereoisomeric mixture of enolates.
  • 42
    • 84918333307 scopus 로고    scopus 로고
    • Compounds 4 and 6 were prepared by selenoxide elimination starting from 2-methylcyclononanone. The resulting mixture was separated by column chromatography on silica gel.
  • 43
    • 84918333306 scopus 로고    scopus 로고
    • 3H) to a 10-membered lactone (30) whose structure was proven by alternative synthesis from (R) citronellol and (S)-propylene oxide.
  • 44
    • 84918333305 scopus 로고    scopus 로고
    • 25
  • 49
    • 84918333304 scopus 로고    scopus 로고
    • 2O), and lactonized as the thiopyridyl ester to give the Baeyer-Villager product of 16.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.