4.6 Article

Diarylprolinol-Mediated Asymmetric Direct Cross-Aldol Reaction of α,β-Unsaturated Aldehyde as an Electrophilic Aldehyde

Journal

CHEMISTRY-AN ASIAN JOURNAL
Volume 14, Issue 23, Pages 4146-4149

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201901236

Keywords

aldehydes; aldol reaction; allyl alcohol; asymmetric synthesis; organocatalysis

Funding

  1. Japan Society for the Promotion of Science [JP19H05630, JP18H04380] Funding Source: Medline

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The diarylprolinol-mediated asymmetric direct cross-aldol reaction of alpha,beta-unsaturated aldehyde as an electrophilic aldehyde was developed. The reaction becomes accelerated by an acid when a carbonyl group is introduced at the gamma-position of the alpha,beta-unsaturated aldehyde. Synthetically useful gamma,delta-unsaturated beta-hydroxy aldehydes were obtained with highanti-selectivity and excellent enantioselectivity.

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