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.
Metal-Free, Regio-and Stereoselective Synthesis of Linear (E)-Allylic Compounds Using C, N, O, and S Nucleophiles. -Bromination of alkenes (I) give the corresponding dibromides which are further converted into linear (E)-allylic compounds upon treatment with various nucleophiles. -(HUANG, X.; FULTON, B.; WHITE, K.; BUGARIN*, A.; Org. Lett. 17 (2015) 11, 2594-2597, http://dx.doi.org/10.1021/acs.orglett.5b00862 ; Dep. Chem. Biochem., Univ. Tex., Arlington, TX 76019, USA; Eng.) -Mais 41-082
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