42842-47-7Relevant academic research and scientific papers
Radical reaction initiated and stereocontrolled by zinc chloride
Yamamoto, Yoshinori,Onuki, Setsuko,Yumoto, Masatoshi,Asao, Naoki
, p. 765 - 780 (1998)
The reaction of allyltributyltin with methyl 2-[N-((4S)-4-(1-methylethyl)-2-oxazolidinone-3-carbamoyl)amino]-2-bromoacetate (5 a) was accelerated at -50°C in the presence of AIBN and stopped in the presence of galvinoxyl, indicating that the reaction proceeds through a radical mechanism. The reaction was accelerated dramatically at -78°C in the presence of ZnCl2·OEt2, and the ZnCl2-mediated reaction was stopped in the presence of galvinoxyl. In the presence of 2 equiv ZnCl2·OEt2, the reaction afforded methyl (2R)-2-[N-((4SH-(1-methylethyl)-2-oxazolidinone-3-carbamoyl)amino]-4-pentenoate {6a(R)} with high diastereoselectivity (93:7). Taken together, ZnCl2·OEt2 works as a radical initiator as well as chelating agent.
Regioselective cross-coupling of allylindium reagents with activated benzylic bromides-a simple and efficient procedure for the synthesis of terminal alkenes
Ranu, Brindaban C.,Banerjee, Subhash,Adak, Laksmikanta
, p. 7374 - 7379 (2008/03/13)
Allylindium reagents undergo facile and highly regioselective cross-coupling with benzylic and cinnamyl bromides in THF at room temperature without any catalyst producing terminal alkenes in high yields. The addition is highly regioselective and is found to provide γ-adducts in all reactions.
