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Volumn 44, Issue 40, 2005, Pages 6576-6579

Catalytic enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes by using a simple thiourea organocatalyst

Author keywords

Asymmetric synthesis; Electrophilic substitution; Hydrogen bonds; Indoles; Organocatalysis

Indexed keywords

CATALYSIS; DERIVATIVES; HYDROGEN BONDS; NITROGEN COMPOUNDS; SYNTHESIS (CHEMICAL);

EID: 27144518078     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200500227     Document Type: Article
Times cited : (483)

References (51)
  • 1
    • 0001586671 scopus 로고
    • Friedel-Crafts Alkylation
    • (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1st ed.
    • a) "Friedel-Crafts Alkylation": G. A. Olah, R. Krishnamurty, G. K. S. Prakash in Comprehensive Organic Synthesis, Vol. III (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1st ed., 1991, p. 293;
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 293
    • Olah, G.A.1    Krishnamurty, R.2    Prakash, G.K.S.3
  • 36
    • 0009492483 scopus 로고
    • for other examples of non-stereoselective Friedel - Crafts additions to nitroalkenes, see: b) W. E. Noland, P. J. Hartman, J. Chem. Soc. 1954, 76, 3227;
    • (1954) J. Chem. Soc. , vol.76 , pp. 3227
    • Noland, W.E.1    Hartman, P.J.2
  • 43
    • 27144505836 scopus 로고    scopus 로고
    • note
    • An alkyl substituent on the indolic nitrogen atom is not tolerated in this catalytic enantioselective reaction, as the addition of N-methylindole to 3a catalyzed by 1d gave the product in good yield (75%) but in a nearly racemic form (6% ee) under the optimized reaction conditions.
  • 44
    • 27144524309 scopus 로고    scopus 로고
    • note
    • The yield of the Friedel-Crafts alkylation of 2a with 3e could be considerably increased by simply performing the reaction at higher temperatures, and only a moderate loss of enantioselectivity in the product 4h occurs (0°C, 76% yield, 72% ee).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.