833454-99-2Relevant academic research and scientific papers
The absolute configuration of (+)- And (-)-1-phenylundec-4-yn-3-ols. Synthesis of (R)-4-dodecanolide, a component of the defensive secretion of rove beetle Bledius mandibullaris
Vlasyuk,Voblikova,Gamalevich,Serebryakov
, p. 2032 - 2036 (2014/07/07)
Hydrogenation of the triple bond of (+)-1-phenylundec-4-yn-3-ol (obtained from (+)[η6 (3-hydroxyundec-4-yn-1-yl)benzene]chromium tricarbonyl) with the NaBH4-NiCl2?6H2O reagent system in MeOH leads to (-)1-phenylundecan-3-ol. Ozonolysis of the phenyl ring in the corresponding acetate gives (R)-(-)acetoxydodecanoic acid, lactonization of which leads to the known (R)-(+)-4dodecanolide. The starting (+)-1phenylundec-4-yn-3-ol was thus shown to have the Sconfiguration.
Highly enantioselective addition of linear alkyl alkynes to linear aldehydes
Du, Yuhao,Turlington, Mark,Zhou, Xiang,Pu, Lin
experimental part, p. 5024 - 5027 (2011/02/22)
It is discovered that the use of biscyclohexylamine (Cy2NH) as an additive can greatly enhance the enantioselectivity for the reaction of linear alkyl alkynes with linear aldehydes. The combination of (S)-BINOL (20 mol %), Cy2NH (5 mol %), ZnEt2 (2 equiv), and Ti(OiPr) 4 (0.5 equiv) catalyzes the reaction at room temperature in diethyl ether solution with 81-89% ee and 57-77% yield.
