CHEMISTRY: Giving Friedel-Crafts a Hand

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Science  27 Apr 2001:
Vol. 292, Issue 5517, pp. 603d
DOI: 10.1126/science.292.5517.603d

One of the most versatile methods for adding a carbon-carbon bond to an aromatic ring is Friedel-Crafts alkylation, in which a Lewis acid (such as AlCl3) catalyzes the addition of an electron-deficient s- or p-bonded compound. However, most variants of this venerable reaction are not stereoselective when adding more complex unsaturated species, such as a,b-unsaturated aldehydes.

Paras and MacMillan now show that reaction of pyrroles with a,b-unsaturated aldehydes in the presence of a chiral amine (a benzyl imidazolidinone) and acid co-catalysts leads to stereospecific addition (typically 90% enantiomeric excess) to the C=C bond. This pathway is favored over the conventional acid-catalyzed pathway that would add to the C=O bond, and the benzyl group helps direct the pyrrole to adding to the si-face. The reaction is quite tolerant of substituents on the pyrrole ring as well as the N-alkyl group, and of various terminal groups on the aldehyde. — PDS

Acknowledgments

J. Am. Chem. Soc., in press.

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