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Volumn 7, Issue 5, 2005, Pages 901-904

Enantioselective Friedel-Crafts alkylation reactions catalyzed by a chiral nonracemic C2-symmetric 2,2′-bipyridyl copper(II) complex

Author keywords

[No Author keywords available]

Indexed keywords

BIPYRIDINE DERIVATIVE; COPPER COMPLEX; ESTER DERIVATIVE; INDOLE DERIVATIVE; LIGAND; PROPIONIC ACID DERIVATIVE; PYRUVIC ACID DERIVATIVE;

EID: 15044357098     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050075d     Document Type: Article
Times cited : (112)

References (26)
  • 4
    • 0001827606 scopus 로고
    • Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon Press: Oxford
    • For discussions on the coordination chemistry of 2,2′-bipyridines and 1,10-phenanthrolines, see: (a) Reedijk, J. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon Press: Oxford, 1987; Vol. 2, pp 73-98.
    • (1987) Comprehensive Coordination Chemistry , vol.2 , pp. 73-98
    • Reedijk, J.1
  • 14
    • 15044345855 scopus 로고    scopus 로고
    • note
    • The F-C reaction of indole 3a with methyl 3,3,3-trifluoropyruvate 4b afforded the product 5b in good yield in dichloromethane and in tetrahydrofuran. However, the enantioselectivities were lower (28 and 45% ee, respectively) in these instances.
  • 15
    • 15044359675 scopus 로고    scopus 로고
    • note
    • The absolute stereochemistry of (2S)-2-(4-chloroindole-3-yl)-3,3,3- trifluoro-2-hydroxy propionic acid ethyl ester has been assigned unambiguously by X-ray crystallography, and the absolute stereochemistry of compound 5a was assigned by analogy; see ref 6b.
  • 16
    • 15044356937 scopus 로고    scopus 로고
    • note
    • This result is in contrast to the bisoxazoline copper(II) complex-catalyzed reactions in which substitution of the indole nitrogen does not lower the enantioselectivity of the reaction; see ref 6b.
  • 19
    • 15044359185 scopus 로고    scopus 로고
    • note
    • See the supporting information for ref 10.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.