Direct Catalytic Asymmetric Enolexo Aldolizations

Pidathala, Chandrakala; Hoang, Linh; Vignola, Nicola; List, Benjamin

doi:10.1002/anie.200351266

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Direct Catalytic Asymmetric Enolexo Aldolizations

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Pidathala, C., Hoang, L., Vignola, N., & List, B. (2003). Direct Catalytic Asymmetric Enolexo Aldolizations. Angewandte Chemie International Edition, 42(24), 2785-2788. doi:10.1002/anie.200351266.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-A4C0-6

Abstract

32 years after the first, and still the only, catalytic asymmetric intramolecular aldol reaction was published in this journal, the proline‐catalyzed Hajos–Parrish–Eder–Sauer–Wiechert reaction is extended for the first time to catalytic asymmetric enolexo aldolizations. The process provides substituted cyclohexanes in excellent diastereo‐ and enantioselectivities. For example, heptanedial is converted into the corresponding cyclic anti‐configured aldol in 99 % ee (see scheme).