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Volumn 63, Issue 24, 1998, Pages 8682-8688

Conformational analysis of 1-(alkoxymethyl)-5(R)-methyl-2-pyrrolidinone derivatives. Determination of the absolute stereochemistry of alcohols

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE; ALCOHOL DERIVATIVE; N (ALKOXYMETHYL) 2 PYRROLIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0031766249     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980029+     Document Type: Article
Times cited : (12)

References (35)
  • 12
    • 0028226105 scopus 로고
    • (b) Rieser, M.; Hui, Y.; Rupprecht, J. K.; Kozlowski, J. F.; Wood, K. V.; McLaughlin, J. L.; Hanson. P. R.; Zhuang, Z.; Hoye, T. R. Ibid. 1992, 114, 10203-10213. Yu, J.-G.; Hu, X.; Ho, D.; Bean, M. F.; Stephens, R. E.; Cassady, J. M. J. Org. Chem. 1994, 59, 1598-1599.
    • (1994) J. Org. Chem. , vol.59 , pp. 1598-1599
    • Yu, J.-G.1    Hu, X.2    Ho, D.3    Bean, M.F.4    Stephens, R.E.5    Cassady, J.M.6
  • 28
    • 15444360037 scopus 로고    scopus 로고
    • note
    • This fact is also in agreement with theory. The geometry of menthol is such that it is hindered from one side, destabilizing the G-form in the adduct from the S enantiomer (see Table 1). This can be seen on the energy contour map (see Figure 5). The linear conformer is more stable, and the barrier to interconversion (G+G-) is higher. The menthol adduct prefers a linear structure.
  • 29
    • 15444342474 scopus 로고    scopus 로고
    • note
    • AB (R) although ΔE(R) < ΔE(S)]. According to calculations, these protons are affected by the shielding/deshielding effects of the aryl ring in a different manner in the respective conformers in R and S (see Figure 6). Figure 6 predicts small differences in the NMR behavior of 5.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.