Catalytic Enantioselective 1,4-Iodofunctionalizations of Conjugated Dienes
Chandra Bhushan Tripathi1, Santanu Mukherjee1
1Department of Organic Chemistry, Indian Institute of Science , Bangalore 560012, India.
Abstract:
The first catalytic enantioselective 1,4-iodofunctionalizations of conjugated dienes have been developed. Starting from β,γ,δ,ε-unsaturated oximes and 4-Ns hydrazones, these N-iodosuccinimide-mediated reactions are catalyzed by newly modified tertiary aminothiourea derivatives and furnish Δ(2)-isoxazoline and Δ(2)-pyrazoline derivatives, respectively, containing an (E)-allyl iodide group at the quaternary stereogenic center generally in high yield and with excellent enantioselectivity (up to 98.5:1.5 er).
Related Concept Videos
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Diels–Alder Reaction: Characteristics of Dienes
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable,...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide


