29727-88-6Relevant academic research and scientific papers
Stereoselective synthesis of nipecotic acid derivatives via palladium-catalyzed decarboxylative cyclization of γ-methylidene-δ- valerolactones with imines
Shintani, Ryo,Murakami, Masataka,Hayashi, Tamio
supporting information; experimental part, p. 457 - 459 (2009/07/11)
(Chemical Equation Presented) A new synthetic method of multisubstituted nipecotic acid (piperidine-3-carboxylic acid) derivatives has been developed by way of palladium-catalyzed decarboxylative cyclization of γ-methylidene- δ-valerolactones with (mines.
Reactivity and diastereoselectivity in the thermal and Lewis acid- catalyzed Diels-Alder reactions of N-sulfinylphosphoramidates
Zhang,Flann
, p. 1372 - 1378 (2007/10/03)
The [4 + 2] cycloaddition reactions of N-sulfinylphosphoromidates, prepared from the corresponding phosphoramidates by treatment with N- (chlorosulfinyl)imidazole, and 1,3-cyclohexadiene were found to be diastereoselective in the absence (>90:10) and presence (> 95:5) of Lewis acid. The sulfur configuration of the major adduct from the cycloaddition reaction has been established unambiguously by X-ray crystallography. The use of Lewis acids improved the diastereoselectivity and yield, as Well as shortened reaction times. Based on the intermediacy of a tin chelate, and the absence of phosphoryl secondary orbital interactions, a mechanism for the cycloaddition reactions is discussed.
