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Volumn 129, Issue 15, 2007, Pages 4506-4507

An experimental and computational study of stereoselectivity and reactivity in Lewis acid promoted lithiation-substitution of tertiary amines

Author keywords

[No Author keywords available]

Indexed keywords

LEWIS ACID; LITHIUM; TERTIARY AMINE;

EID: 34247527763     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0675144     Document Type: Article
Times cited : (28)

References (33)
  • 1
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    • and references cited therein
    • Kessar, S. V.; Singh, P. Chem. Rev. 1997, 97, 721 and references cited therein.
    • (1997) Chem. Rev , vol.97 , pp. 721
    • Kessar, S.V.1    Singh, P.2
  • 6
    • 0032517369 scopus 로고    scopus 로고
    • For seminal work on Lewis acid promoted deprotonative chemistry in gas phase see
    • For seminal work on Lewis acid promoted deprotonative chemistry in gas phase see: Ren, J.; Workman, D. B.; Squires, R. R. J. Am. Chem. Soc. 1998, 120, 10511-10522.
    • (1998) J. Am. Chem. Soc , vol.120 , pp. 10511-10522
    • Ren, J.1    Workman, D.B.2    Squires, R.R.3
  • 11
    • 34247467861 scopus 로고    scopus 로고
    • CSP HPLC was carried out on a Chiralcell OD column
    • (a) CSP HPLC was carried out on a Chiralcell OD column.
  • 12
    • 34247537069 scopus 로고    scopus 로고
    • Yields are based on isolated products not taking into account the balance starting material and no basic side products were detected
    • (b) Yields are based on isolated products not taking into account the balance starting material and no basic side products were detected.
  • 13
    • 33747761620 scopus 로고    scopus 로고
    • Interconversion of enantiomeric α-lithiated N-ethyl pyrrolidines, accessed through a multistep sequence, shows similar temperature dependence. (a) Coldham, I.; Dufour, S.; Haxel, T. F. N.; Patel, J. J.; Jimenez, G. S. J. Am. Chem. Soc. 2006, 128, 10943.
    • Interconversion of enantiomeric α-lithiated N-ethyl pyrrolidines, accessed through a multistep sequence, shows similar temperature dependence. (a) Coldham, I.; Dufour, S.; Haxel, T. F. N.; Patel, J. J.; Jimenez, G. S. J. Am. Chem. Soc. 2006, 128, 10943.
  • 15
    • 34247513346 scopus 로고    scopus 로고
    • 3 complexed α-lithiated phospholanes undergo rapid syn-anti conversion even at -100° C (see ref. 9).
    • 3 complexed α-lithiated phospholanes undergo rapid syn-anti conversion even at -100° C (see ref. 9).
  • 16
    • 34247533630 scopus 로고    scopus 로고
    • 3 complexes.
    • 3 complexes.
  • 17
    • 34247514674 scopus 로고    scopus 로고
    • 2CN complexes failed (see Supporting Information).
    • 2CN complexes failed (see Supporting Information).
  • 19
    • 34247479364 scopus 로고    scopus 로고
    • 3 complexes.
    • 3 complexes.
  • 20
    • 34247481777 scopus 로고    scopus 로고
    • CCDC No. 619876
    • (a) CCDC No. 619876.
  • 21
    • 34247548227 scopus 로고    scopus 로고
    • See Supporting Information also
    • (b) See Supporting Information also.
  • 22
    • 34247549571 scopus 로고    scopus 로고
    • However, with a warm-cool cycle, formation of diastereomeric products and the lowering of 10 er (56:44) is observed.
    • (a) However, with a warm-cool cycle, formation of diastereomeric products and the lowering of 10 er (56:44) is observed.
  • 23
    • 34247528889 scopus 로고    scopus 로고
    • The yield based on kinetic resolution of racemic 9a is 56%. No alternate procedure for α-substitution of amino ring juncture, a feature present in a variety of alkaloids, is available.
    • (b) The yield based on kinetic resolution of racemic 9a is 56%. No alternate procedure for α-substitution of amino ring juncture, a feature present in a variety of alkaloids, is available.
  • 24
    • 34247466355 scopus 로고    scopus 로고
    • It also emphasizes the need of more refined solvent treatment, desirably taking into account local and bulk effects, in computations of lithiation-substitution chemistry especially when the observed selectivity is opposite to gas phase predictions or is seemingly counterintuitive. (a) Topics in Organnometullic Chemistry; Springer-Verlag: 2003; 5, pp 1-310.
    • It also emphasizes the need of more refined solvent treatment, desirably taking into account local and bulk effects, in computations of lithiation-substitution chemistry especially when the observed selectivity is opposite to gas phase predictions or is seemingly counterintuitive. (a) Topics in Organnometullic Chemistry; Springer-Verlag: 2003; Vol. 5, pp 1-310.
  • 32
  • 33
    • 34247480818 scopus 로고    scopus 로고
    • This supports the role of Li-F interaction in BF3 effectiveness
    • 3 effectiveness.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.