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Volumn 349, Issue 11-12, 2007, Pages 1863-1867

Chiral phosphoric acid-catalyzed enantioselective aza-Friedel-Crafts reaction of indoles

Author keywords

Asymmetric catalysis; Br nsted acid; Enantioselectivity; Friedel Crafts reaction; Organic catalysis; Phosphoric acid

Indexed keywords


EID: 34548378986     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200700151     Document Type: Article
Times cited : (150)

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    • The F-C reaction of N-unprotected indole with N-Boc imine (3a) took place immediately at room temperature without any catalysts. To suppress this uncatalyzed pathway in the F-C reaction, we initially explored N-protected indoles (2). After several trials, the tert-butyldimethylsilyl group found to be the best, where a trace amount of the F-C product was obtained without catalysts even at room temperature for 24 h; see Supporting Information for details.
    • The F-C reaction of N-unprotected indole with N-Boc imine (3a) took place immediately at room temperature without any catalysts. To suppress this uncatalyzed pathway in the F-C reaction, we initially explored N-protected indoles (2). After several trials, the tert-butyldimethylsilyl group found to be the best, where a trace amount of the F-C product was obtained without catalysts even at room temperature for 24 h; see Supporting Information for details.
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    • We also examined computational analysis of hydrogen-bonding pairs of the catalysts (1) with N-Boc imines (3) at the B3LYP/6-31G** level of theory. See Supporting Information for details
    • We also examined computational analysis of hydrogen-bonding pairs of the catalysts (1) with N-Boc imines (3) at the B3LYP/6-31G** level of theory. See Supporting Information for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.