Catalytic Asymmetric Intramolecular α-Alkylation of Aldehydes
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- 17 December 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (2) , 450-451
- https://doi.org/10.1021/ja0392566
Abstract
The development of a general catalytic asymmetric aldehyde α-alkylation reaction constitutes a major challenge in organic synthesis. Here, we report the first and successful approach toward its solution: (S)-α-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.Keywords
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