Organic Chemistry, Natural Products, Synthesis, Methodology

Catalytic Enantioselective Friedel-Crafts Alkylations of Indoles with alpha’-Phosphoric Enones

Link: Org Lett ASAP

Hyeyeon Yang, Young-Taek Hong, and Sunggak Kim*

Center for Molecular Design & Synthesis and Department of Chemistry, School of Molecular Science, Korea Advanced Institute of Science and Technology, Daejeon 305-701, Korea

Friedel-Crafts alkylation of indoles and pyrrole was accomplished. The catalyst for this reaction is the copper-py-box complex 1a and the alkyl counterparts were the alpha’-phosphate enones. Both indoles and pyrrole were alkylated at the 3-position on the ring.

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The reaction was best conducted in CH2Cl2 at low temperatures. The reaction was applicable to a wide variety of both indoles and enones as shown in Tables 2 and 3. As can be seen, the reaction afforded the products in excellent yields and ees.

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The reaction also worked well with N-methyl pyrrole.

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The products could be elaborated in subsequent reactions as shown in equations below.

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The mechanism of this reaction has been well-studied and it is represented in theĀ figure below.

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May 21, 2007 - Posted by | Methodology

3 Comments »

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