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Volumn 127, Issue 27, 2005, Pages 9924-9929

Stereochemical memory effects in alkene radical cation/anion contact ion pairs: Effect of substituents, and models for diastereoselectivity

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; BENZENE; KETONES; MATHEMATICAL MODELS; OLEFINS; STRAIN RATE; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 22144432606     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja051657t     Document Type: Article
Times cited : (23)

References (55)
  • 11
  • 16
    • 0001271574 scopus 로고    scopus 로고
    • Renaud, P., Sibi, M., Eds.; Wiley-VCH: Weinheim
    • (b) Crich, D. In Radicals in Organic Synthesis; Renaud, P., Sibi, M., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, p 188.
    • (2001) Radicals in Organic Synthesis , vol.2 , pp. 188
    • Crich, D.1
  • 37
    • 22144489616 scopus 로고    scopus 로고
    • note
    • In this paper, nitrophosphates and their precursors are numbered as indicated. The N-benzyl group is considered part of the extended zigzag conformation backbone, and all methyl groups are considered substituents. For purposes of consistency throughout the paper, this system is applied even to compounds 3, 5, and 6, which would be more correctly shown with the methyl group as part of the backbone and the amine as a substituent. (diagram presented)
  • 38
    • 22144466670 scopus 로고    scopus 로고
    • note
    • No significant difference was observed on the product ratios, whether determined on the crude reaction mixtures or following the extractive workup.
  • 40
    • 22144459531 scopus 로고    scopus 로고
    • note
    • 14
  • 41
    • 22144487829 scopus 로고    scopus 로고
    • note
    • In the trisubstituted pyrrolidines 11-13, the first stereochemical descriptor refers to the relationship between the isopropyl group on the 2-position and the next substituent around the ring. The second stereochemical descriptor applies to the relationship between the two methyl groups; thus, for example, cis,trans-11 refers to 2,3-cis-3,4-trans-1-benzyl-2-isopropyl-3,4- dimethylpyrrolidine.
  • 42
    • 22144437849 scopus 로고    scopus 로고
    • note
    • It should be noted, however, that 1,3-diaxial interactions are less important in chair-like transition states with their longer partial bonds than in actual chair form rings, which leaves open the possibility that these cyclizations may occur through the chair-like transition states.
  • 43
    • 22144478019 scopus 로고    scopus 로고
    • note
    • In this scheme, anti,anti-6 and trans,cis-13, and the associated transition states, are represented as their enantiomers for ease of comparison.
  • 49
    • 0000782249 scopus 로고    scopus 로고
    • Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim
    • (b) Newcomb, M. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 1, p 317.
    • (2001) Radicals in Organic Synthesis , vol.1 , pp. 317
    • Newcomb, M.1
  • 55
    • 22144459907 scopus 로고    scopus 로고
    • note
    • Presumably, these oxidative cyclizations take place at the level of the pyrrolidinium ion arising from the first cyclization, suggesting that the configuration at nitrogen and possibly even the bulk: of the associated phosphate anion must be taken into account in any model.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.