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Volumn 15, Issue 9, 2009, Pages 2055-2058

Enantioselective Friedel-Crafts alkylation of indoles with alkylidene malonates catalyzed by N,N′-dioxide-scandium(III) complexes: Asymmetric synthesis of β-carbolines

Author keywords

Alkylidene malonates; Asymmetric synthesis; Friedel Crafts alkylation; Indole derivatives; Scandium

Indexed keywords

ALKYLATION; AMIDES; AMINES; AMINO ACIDS; BROMINE; COMPLEXATION; CRYSTAL STRUCTURE; ELECTRON TRANSITIONS; ENANTIOSELECTIVITY; HYDROCARBONS; ORGANIC ACIDS; SCANDIUM; SUGAR (SUCROSE);

EID: 60749133070     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200802210     Document Type: Article
Times cited : (115)

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    • Different standard reaction parameters (solvent, Lewis acid) were also evaluated during the optimization of the process see Supporting Information for details
    • Different standard reaction parameters (solvent, Lewis acid) were also evaluated during the optimization of the process (see Supporting Information for details).
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    • Excess indole could be recycled by flash chromatography on silica gel
    • Excess indole could be recycled by flash chromatography on silica gel.
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    • In the catalytic systems of chiral Cu″-oxazoline, ortho-substituted and para-substituted arylidene malonates gave very good results but meta-substituted arylidene malonates were not tolerated see references [6-8] for details
    • In the catalytic systems of chiral Cu″-oxazoline, ortho-substituted and para-substituted arylidene malonates gave very good results but meta-substituted arylidene malonates were not tolerated (see references [6-8] for details).
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    • It was probably attributed to the steric hindrance effect of the ortho-substituent on phenyl in arylidene malonate
    • It was probably attributed to the steric hindrance effect of the ortho-substituent on phenyl in arylidene malonate.
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    • Alkylidene malonates were also investigated, but only moderate results were obtained (propylidene malonale: 32% yield, 66% ee: cyclohexylmethylene malonate: 57% yield, 43% ee).
    • Alkylidene malonates were also investigated, but only moderate results were obtained (propylidene malonale: 32% yield, 66% ee: cyclohexylmethylene malonate: 57% yield, 43% ee).
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    • See Supporting Information for details
    • See Supporting Information for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.