Conjugate Addition Reactions Mediated by Samarium(II) Iodide
Gary A. Molander1, Christina R. Harris
1Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215.
Abstract:
Samarium(II) iodide in conjunction with a catalytic low-valent transition metal species has been employed to promote the conjugate addition reaction of primary and secondary alkyl halides onto alpha,beta-unsaturated esters and amides. The method has been determined to be quite general and hence has been extended to the cyclization reactions of alkyl halides onto alpha,beta-unsaturated lactones, lactams, and nitriles. The cyclization reactions described herein provide a very general approach to the synthesis of functionalized carbocycles from simple acyclic precursors with excellent diastereoselectivity and under very mild reaction conditions.
More Related Videos
07:50Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
10:42Combining Solid-state and Solution-based Techniques: Synthesis and Reactivity of Chalcogenidoplumbates(II or IV)
Published on: December 29, 2016
Related Concept Videos
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Conjugate Addition of Enolates: Michael Addition
Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)
Conjugate addition results in a thermodynamically stable product. The reaction retains the stronger C=O bond at the expense of the weaker C=C π bond. The process is slow as the β carbon is less electrophilic than the carbonyl carbon.
Direct addition products are formed faster owing to...
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Cycloaddition Reactions: Overview
Cycloaddition Reactions: MO Requirements for Thermal Activation
