메뉴 건너뛰기




Volumn 127, Issue 47, 2005, Pages 16406-16407

Enantioselective protonation of catalytically generated chiral enolates as an approach to the synthesis of α-chloroesters

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA CHLOROESTER DERIVATIVE; ESTER DERIVATIVE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

EID: 28444444128     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja055918a     Document Type: Article
Times cited : (250)

References (34)
  • 1
    • 0002652021 scopus 로고
    • Morrison, J. D., Ed.; Academic Press: New York
    • (a) Evans, D. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, p 1.
    • (1984) Asymmetric Synthesis , vol.3 , pp. 1
    • Evans, D.A.1
  • 2
  • 25
    • 3042770459 scopus 로고    scopus 로고
    • Substrate control in the diastereoselective protonation of similar intermediates has been demonstrated: Chow, K. Y.-K.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 8126-8127.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 8126-8127
    • Chow, K.Y.-K.1    Bode, J.W.2
  • 27
    • 28444480603 scopus 로고    scopus 로고
    • note
    • 2,2-Dichloro-(S)-citronellal provides the product in 19% yield and 9:1 dr.
  • 30
    • 28444438448 scopus 로고    scopus 로고
    • note
    • Achiral catalyst: (Diagram presented).
  • 31
    • 0004391592 scopus 로고
    • A values: Br = 0.7; Me = 1.6-1.8. van der Waals radii: Br = 1.95; Me = 2.0. C-X bond lengths: Br = 1.94; Me = 1.54. See: Eliel, E. R.; Haber, R. G. J. Am. Chem. Soc. 1959, 81, 1249-1254.
    • (1959) J. Am. Chem. Soc. , vol.81 , pp. 1249-1254
    • Eliel, E.R.1    Haber, R.G.2
  • 32
    • 0037462584 scopus 로고    scopus 로고
    • a values: 2-methylphenol = 10.32; 2,6-dibromophenol = 6.6. See: Hanai, T. J. Chromatogr. A 2003, 985, 343-349.
    • (2003) J. Chromatogr. A , vol.985 , pp. 343-349
    • Hanai, T.1
  • 34
    • 28444471145 scopus 로고    scopus 로고
    • note
    • Under the reported conditions, using 5 mol % of A (1.42 g) and 1a (60 mmol) provided 8.67 g of 2a (55% yield) with 90% ee (62% recovery of excess PhOH).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.