Diastereoselective Substitution Reactions of Acyclic β-Alkoxy Acetals via Electrostatically Stabilized Oxocarbenium Ion Intermediates.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c01004
Abstract: Substitution reactions of acyclic β-alkoxy acetals proceeded with generally high diastereoselectivities (>90:10) to form the anti product. Mechanistic experiments supplemented with computational studies suggest that, upon activation of the acetal, the resulting oxocarbenium ion is… read more here.
Keywords: oxocarbenium ion; reactions acyclic; electrostatically stabilized; acyclic alkoxy ... See more keywords
Borane-Catalyzed Direct Asymmetric Vinylogous Mannich Reactions of Acyclic α,β-Unsaturated Ketones.
Sign Up to like & getrecommendations! Published in 2021 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.1c00006
Abstract: Herein, we report that, by using chiral bicyclic bisborane catalysts, we have achieved the first highly regio-, diastereo-, and enantioselective direct asymmetric vinylogous Mannich reactions of acyclic α,β-unsaturated ketones. The strong Lewis acidity and steric… read more here.
Keywords: acyclic unsaturated; direct asymmetric; asymmetric vinylogous; reactions acyclic ... See more keywords