63399-86-0Relevant academic research and scientific papers
Highly Stereoselective Synthesis of Chiral Alkylallenes by Organocopper(I)-Induced Anti 1,3-Substitution of Chiral Propynyl Esters
Elsevier, Cornelis J.,Vermeer, Peter
, p. 3726 - 3730 (1989)
The synthesis of chiral 1,3-dialkylallenes R1CH=C=CHR2 of high enantiomeric purity, by applying homogeneous reaction between organocopper(I) reagents of type 2CuX>MgX-LiX> and chiral propynyl methanesulfonates or sulfinates at low temperatures in THF, is reported.The reactions are generally fast; typically complete conversion is obtained within a few minutes at -60 deg C.Overall, high anti stereoselectivity is observed.A plausible mechanism is put forward, and comparison is made with the stereochemistry of reactions of comparable substrates with d10 complexes, e.g. of Pd(0).
