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ChemInform Abstract: Metal-Free, Regio- and Stereoselective Synthesis of Linear (E)-Allylic Compounds Using C, N, O, and S Nucleophiles
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ChemInform Abstract: Metal-Free, Regio- and Stereoselective Synthesis of Linear (E)-Allylic Compounds Using C, N, O, and S Nucleophiles

Xiaojun Huang, Brandon Fulton, Kana White and Alejandro Bugarin
OrganicLetters, Vol.46(41), pp.no-no
10-2015
PMID: 25965247

Abstract

carboxylic acid esters (acyclic compounds) carboxylic acid esters (benzene compounds) carboxylic amides (acyclic compounds) carboxylic amides (benzene compounds) e/z-selectivity (incl. e/z-isomerism) thio compounds (acyclic compounds) thio compounds (benzene compounds)
A variety of allylic acetates and derivatives were synthesized by an efficient two-step protocol that employs readily available terminal alkenes as starting materials. This method is highly regio- and stereoselective, affording the linear (E)- isomer as the sole adduct. This process tolerates several functional groups including halogen-containing molecules, and it is general for weak oxygen, carbon, nitrogen, and sulfur nucleophiles. Furthermore, adducts were obtained in good to excellent yields.
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