136265-15-1Relevant academic research and scientific papers
Stereochemistry of the Reaction of Diorganocuprate(I) Complexes Derived from Grignard Reagents with α,β-Acetylenic Esters
Jalander, Lars,Iambolieva, Kostadinka,Sundstroem, Viola
, p. 715 - 720 (2007/10/02)
Diorganocuprate(I) complexes RCH3CuMgX, prepared from methylcopper and Grignard reagents (i-PrMgBr and t-BuMgCl) gave mainly cis-1,4-addition of the alkyl group originally present in the Grignard reagents and small amounts of cis- and trans-1,4-addition of the methyl group introduced by methylcopper, when they were allowed to react with ethyl propiolate and ethyl phenylpropiolate.The proportion of cis-1,4-addition products did not change when the reaction temperature was raised from -78 deg C to room temperature.The configurations of the main reaction products from the reaction with ethyl phenylpropiolate, ethyl (Z)-β-isopropylcinnamate and ethyl (Z)-β-t-butylcinnamate, were established by conversion of the corresponding acids to β-isopropylindenone and β-t-butylindenone.
