Journal of the American Chemical Society

Catalytic asymmetric intramolecular α-alkylation of aldehydes

N Vignola, B List

Index: Vignola, Nicola; List, Benjamin Journal of the American Chemical Society, 2004 , vol. 126, # 2 p. 450 - 451

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Citation Number: 212

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, ...