262586-82-3Relevant academic research and scientific papers
Efficient enantioselective additions of terminal alkynes and aldehydes under operationally convenient conditions
Boyall, Dean,Frantz, Doug E.,Carreira, Erick M.
, p. 2605 - 2606 (2002)
(Matrix presented) The enantioselective addition reaction of terminal acetylenes and aldehydes mediated by Zn(OTf)2 and N-methyl ephedrine can be conducted with reagent grade solvent containing 84-1000 ppm H2O. The products can be is
Catalytic asymmetric enyne addition to aldehdyes and Rh(I)-catalyzed stereoselective domino Pauson-Khand/[4 + 2] cycloaddition
Chen, Wei,Tay, Jia-Hui,Ying, Jun,Yu, Xiao-Qi,Pu, Lin
, p. 2256 - 2265 (2013/04/24)
The 1,1′-bi-2-naphthol-ZnEt2-Ti(OiPr) 4-Cy2NH system is found to catalyze the 1,3-enyne addition to aliphatic aldehydes as well as other aldehydes at room temperature with 75-96% yield and 82-97% ee. This system is also broadly applicable for the highly enantioselective reaction of other alkyl-, aryl-, and silylalkynes with structurally diverse aldehydes. The propargylic alcohols prepared from the catalytic asymmetric enyne addition to aliphatic aldehydes are used to prepare a series of optically active trienynes. In the presence of a catalytic amount of [RhCl(CO)2]2 and 1 atm of CO, the optically active trienynes undergo highly stereoselective domino Pauson-Khand/[4 + 2] cycloaddition to generate optically active multicyclic products. The Rh(I) catalyst is also found to catalyze the coupling of a diyne with CO followed by [4 + 2] cycloaddition to generate an optically active multicyclic product. These transformations are potentially useful for the asymmetric synthesis of polyquinanes containing a quaternary chiral carbon center.
