Enantioselective zirconium-catalyzed Friedel-Crafts alkylation of pyrrole with trifluoromethyl ketones

Organic Letters
Gonzalo BlayCarlos Vila

Abstract

The first catalytic enantioselective Friedel-Crafts alkylation of pyrrole with 2,2,2-trifluoroacetophenones to give pyrroles with a trifluoromethyl-substituted tertiary alcohol moiety bearing a quaternary stereogenic center is described. The reaction is achieved in the presence of a 3,3'-dibromo-BINOL-Zr(IV) complex to give the expected products with high yields (up to 98%) and good enantioselectivities (up to 93% ee). The absolute stereochemistry of the products has been determined by chemical correlation.

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Citations

Mar 4, 2010·Chemical Communications : Chem Comm·Srinath ThirumalairajanAlison Thompson
Oct 29, 2013·Chemical Communications : Chem Comm·Christopher B KellyNicholas E Leadbeater
Nov 13, 2013·Organic & Biomolecular Chemistry·Sanjeev P Mahanta, Pradeepta K Panda
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Mar 16, 2011·Chemistry : a European Journal·Teruhisa Tsuchimoto
Jan 21, 2014·Chemical Communications : Chem Comm·Amparo Sanz-MarcoJosé R Pedro
Mar 3, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Mandeep Kaur HunjanJoydev K Laha
Jul 31, 2009·The Journal of Organic Chemistry·Yi-Fei ShengShu-Li You
Apr 13, 2012·The Journal of Organic Chemistry·Yilin LiuHaifeng Du

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