Journal
CHEMICAL SCIENCE
Volume 12, Issue 4, Pages 1445-1450Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0sc05269h
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Funding
- JSPS KAKENHI [JP26220803, JP18H01975, JP20H04815]
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This study demonstrated a highly diastereodivergent synthesis of beta-amino aldehydes with a chiral alpha-tert-amine moiety, utilizing less-activated Z-ketimines in amine-catalyzed Mannich reactions with aldehydes. This method overcame the limitations of structural variations in ketimines, achieving high diastereoselectivity.
Stereoselective Mannich reactions of aldehydes with ketimines provide chiral beta-amino aldehydes that bear an alpha-tert-amine moiety. However, the structural variation of the ketimines is limited due to the formation of inseparable E/Z isomers, low reactivity, and other synthetic difficulties. In this study, a highly diastereodivergent synthesis of hitherto difficult-to-access beta-amino aldehydes that bear a chiral alpha-tert-amine moiety was achieved using the amine-catalyzed Mannich reactions of aldehydes with less-activated Z-ketimines that bear both alkyl and alkynyl groups.
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