Highly regioselective and stereoselective cascade reductive cyclization of δ-ketoamide: practical access to
Hao Ye1, Xi-Wei Zhu1, Yi-Yun Pan1
1College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, P. R. China. wuxinxng@163.com.
Abstract:
A highly regioselective and stereoselective cascade reduction cyclization of δ-ketoamide is realized under LiAlH4-assisted conditions, providing an atom-economical and straightforward approach to access oxa-bridged benzazepines in moderate to good yields. This method overcomes the limitations of aldehydes or other precursors of primary alcohols and realizes the cascade reduction cyclization of secondary alcohol anions generated in situ from ketones. The reaction proceeds with broad substrate scope and good functional group compatibility.
Related Concept Videos
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation
As the self-condensation of ketones is generally not favored in basic conditions, the self-condensed products do not form in the reaction between ketones and benzaldehyde. The general reaction of Claisen–Schmidt...
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation
The carbonyl center is...
Reactions at the Benzylic Position: Oxidation and Reduction

![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
