76711-55-2Relevant academic research and scientific papers
Lewis Acid Mediated Reactions of Organocopper Reagents. Entrainment in the Conjugate Addition to α,β-Unsaturated Ketones, Esters, and Acids via the RCu*BF3 System
Yamamoto, Yoshinori,Yamamoto, Sinichi,Yatagai, Hidetaka,Ishihara, Yuji,Maruyama, Kazuhiro
, p. 119 - 126 (2007/10/02)
Lewis acid mediated reactions of organocopper reagents with various kinds of α,β-unsaturated carbonyl derivatives are described.RCu*BF3, as well as RCu-other Lewis acid systems, is useful for the conjugate addition to the α,β-unsaturated ketones and esters, whose double bonds are sterically crowded.Certain α,β-unsaturated carboxylic acids also undergo a 1,4-addition through this reagent.Methyl sorbate undergos a 1,4-addition via BuCu*BF3, while undergoing a 1,6-α,δ-addition via Bu2CuLi.BuCu*BF3 reacts more readily with an aldehyde than with a ketone; the degree of chemoselectivity is greater than that of Bu2CuLi, BuLi, or BuMgBr.The R2CuLi-BF3 system is useful for the double alkylation of α,β-unsaturated esters at the β-position and the carbonyl center.Stereochemical aspects of these new copper reagents are also reported.
EFFICIENT STEREOSELECTIVE SYNTHESIS OF rel-(6S,7S,8S)-7-BUTYL-8-HYDROXY-1-AZASPIROUNDECAN-2-ONE, A KEY INTERMEDIATE FOR PERHYDROHISTRIONICOTOXIN, AND ITS rel-(6R) ISOMER
Ibuka, Toshiro,Minakata, Hiroyuki,Mitsui, Yoshinori,Tabushi, Eiji,Taga, Tooru,Inubushi, Yasuo
, p. 1409 - 1412 (2007/10/02)
Using 3-t-butyldimethylsilyloxy-1-cyclohexenyl methyl ketone as a starting material, a simple stereoselective synthesis of rel-(6S,7S,8S)-7-butyl-8-hydroxy-1-azaspiroundecan-2-one, a useful intermediate for the synthesis of pharmacologically importan
