Switchable multipath cascade cyclization to synthesize bicyclic lactams and succinimides via chemodivergent reaction
Yimei Song1, Chaofei Wu1, Jinhai Zhang1
1College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, 325035, China. hongxin-107@163.com.
Abstract:
Herein, a novel switchable multipath cascade cyclization via chemodivergent reaction between readily available ketoamides and deconjugated butenolides was developed to efficiently synthesize γ-lactone fused γ-lactams and succinimide fused hemiketals. The Aldol/aza-Michael reaction and Aldol/imidation/hemiketalization reaction were enabled by catalytic amounts of two bases, namely tetramethyl guanidine and NaOAc. A wide range of substrate scope with diverse functional group compatibility was demonstrated to deliver the corresponding products with good yield and excellent diastereoselectivity (>60 examples).
Related Concept Videos
Cycloaddition Reactions: Overview
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Cycloaddition Reactions: MO Requirements for Thermal Activation
Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

![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)
