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.


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.



The reaction also worked well with N-methyl pyrrole.


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



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



May 21, 2007 - Posted by | Methodology


  1. very interesting
    enterprise rentacar bologna enterprise rentacar faro

    Comment by Mozuqkkk | August 24, 2007 | Reply

  2. interesting thank you…
    enterprise rentacar sales enterprisecarrental logo

    Comment by Xadeqkkk | August 25, 2007 | Reply

  3. information …

    Comment by Tipyeala | August 28, 2007 | Reply

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )


Connecting to %s

%d bloggers like this: