메뉴 건너뛰기




Volumn 65, Issue 52, 2009, Pages 10917-10929

N,3,4-Trisubstituted pyrrolidines by electron transfer-induced oxidative cyclizations of N-allylic β-amino ester enolates

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; AMINE; BENZENE DERIVATIVE; BETA ALANINE; ESTER DERIVATIVE; FERROCENE DERIVATIVE; PHOSPHATE; PYRROLIDINE DERIVATIVE; RADICAL;

EID: 70449702203     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.10.034     Document Type: Article
Times cited : (18)

References (102)
  • 1
    • 70449719506 scopus 로고    scopus 로고
    • Selected reviews
    • Selected reviews:
  • 8
    • 70449730139 scopus 로고    scopus 로고
    • Selected reviews
    • Selected reviews:
  • 14
    • 70449714066 scopus 로고    scopus 로고
    • Selected reviews
    • Selected reviews:
  • 17
    • 70449728344 scopus 로고    scopus 로고
    • Selected recent reviews
    • Selected recent reviews:
  • 26
    • 70449727268 scopus 로고    scopus 로고
    • Selected recent reviews
    • Selected recent reviews:
  • 31
    • 70449723572 scopus 로고    scopus 로고
    • Selected reviews
    • Selected reviews:
  • 34
    • 70449717714 scopus 로고    scopus 로고
    • Selected recent reviews
    • Selected recent reviews:
  • 41
    • 70449732925 scopus 로고    scopus 로고
    • Selected reviews
    • Selected reviews:
  • 42
  • 44
    • 70449721322 scopus 로고    scopus 로고
    • Selected recent reviews
    • Selected recent reviews:
  • 48
    • 70449717712 scopus 로고    scopus 로고
    • Reviews
    • Reviews:
  • 52
    • 70449700446 scopus 로고    scopus 로고
    • Reviews
    • Reviews:
  • 74
    • 47349116008 scopus 로고    scopus 로고
    • For a recent review on synthetic applications of TEMPO, see:
    • For a recent review on synthetic applications of TEMPO, see:. Vogler T., and Studer A. Synthesis (2008) 1979-1993
    • (2008) Synthesis , pp. 1979-1993
    • Vogler, T.1    Studer, A.2
  • 75
    • 70449704834 scopus 로고    scopus 로고
    • Reviews
    • Reviews:
  • 80
    • 70449717641 scopus 로고    scopus 로고
    • Recent reviews on the persistent radical effect
    • Recent reviews on the persistent radical effect:
  • 83
    • 70449702184 scopus 로고    scopus 로고
    • β-Amino ester enolates have not been investigated in detail with regard to the formation of mixed aggregates with lithium halides, their formation is documented with ketones, see for instance
    • β-Amino ester enolates have not been investigated in detail with regard to the formation of mixed aggregates with lithium halides, their formation is documented with ketones, see for instance:
  • 89
    • 70449723506 scopus 로고    scopus 로고
    • note
    • 1, a=5.5570(2), b=11.8157(3), c=18.5313(4) Å, Z=4, T=100 K. A colorless tablet 0.25×0.15×0.06 mm was used to record a total of 23458 data to 2θ(max) 151° using Cu Kα radiation on an Oxford Diffraction Nova O diffractometer. The structure was refined using the program SHELXL-97 (G.M. Sheldrick, Acta Cryst. 2008, A64, 112-122) to wR2 0.080, R1 0.030 (all data) for 2512 independent data and 155 parameters. The Flack parameter refined to 0.06(18), thus determining the absolute configuration on the basis of the anomalous dispersion of oxygen. Complete crystallographic data have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC 747054. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: (internat.) 1 44 1223/336 033; E-mail: deposit@ccdc.cam.ac.uk].
  • 93
    • 70449700373 scopus 로고    scopus 로고
    • note
    • We thank a referee for the suggestion of 10 acting as a SET oxidant for enolates 7*.
  • 94
    • 70449715853 scopus 로고    scopus 로고
    • note
    • Reagent 3 is stable to storage on the bench for more than 6 months. A gain of weight was not observed during storage. However, 3 is dried routinely prior to use in high vacuum at room temperature for 1-2 h. For the preparation of 3, see: Ref. 25a.
  • 95
    • 0001478790 scopus 로고
    • Kinetics of hydrogen abstraction from THF:
    • Kinetics of hydrogen abstraction from THF:. Newcomb M., and Park S.U. J. Am. Chem. Soc. 108 (1986) 4132-4134
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 4132-4134
    • Newcomb, M.1    Park, S.U.2
  • 96
    • 0005927219 scopus 로고
    • Scheffold R. (Ed), Helvetica Chimica Acta, Basel
    • Heathcock C.H. In: Scheffold R. (Ed). Modern Synthetic Methods (1992), Helvetica Chimica Acta, Basel 1-102
    • (1992) Modern Synthetic Methods , pp. 1-102
    • Heathcock, C.H.1
  • 97
    • 70449731033 scopus 로고    scopus 로고
    • Leading references
    • Leading references:


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.