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J Am Chem Soc. 2004 Jan 21;126(2):450-1.

Catalytic asymmetric intramolecular alpha-alkylation of aldehydes.

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  • 1Max-Planck-Institut für Kohlenforschung, D-45470 Mülheim an der Ruhr, Germany.


The development of a general catalytic asymmetric aldehyde alpha-alkylation reaction constitutes a major challenge in organic synthesis. Here, we report the first and successful approach toward its solution: (S)-alpha-methyl proline catalyzes the intramolecular alkylation of various halo aldehydes to the corresponding formyl cyclopentanes, -cyclopropanes, or -pyrrolidines in excellent yields and enantioselectivities. Most remarkably, racemization, aldolization, or catalyst alkylation do not occur to any significant extend, further illustrating the power, mildness, and profound selectivity of enamine catalysis.

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