WebStructure Distortions in Heteroatom-Substituted Cyclohexanones, Adamantanones, and Adamantanes: Origin of Diastereofacial Selectivity. Chemical Reviews 1999 , 99 (5) , … WebDec 29, 2004 · The diastereofacial selectivity operating in Diels-Alder additions involving spirocyclic cross-conjugated cyclohexadienones with dienes of varying reactivity has been investigated. The study has included the ether series 1a-c as well as the lactone/ketone pair 2a/2b. In all cases, the preferred [4+2] cycloaddition pathway consisted of bonding ...
Theoretical analysis of the regio- and stereoselective ... - Springer
WebFeb 1, 2000 · Temperature‐dependent selectivity in nucleophilic additions is affected by the solvent. The inversion temperature (marked with arrows in the graph) that appears in the nonlinear Eyring plots of ln (anti/syn ) versus temperature for the addition of butyllithium to an O‐protected α‐hydroxy aldehyde 1 does not depend on nucleophiles (n BuLi ( ), t BuLi … WebDec 19, 2024 · The incorporation of geminal dimethyl substitution at C(5) has two effects: (i) it induces a conformational bias on an adjacent, otherwise conformationally labile C(4)-substituent so that it projects towards the N-acyl fragment, thus offering superior diastereofacial selectivity in a range of transformations; and (ii) it hinders nucleophilic ... terminal island 1973 movie
Asymmetric Diels-Alder reaction: applications of chiral dienophiles
WebFacial diastereoselectivity. The 3- and 6-acetoxyvinylcyclohexenes 53 and 54 react with dimethyl-acetylenedicarboxylate to afford bicyclic esters [50]. It is noteworthy that the … WebFeb 1, 2008 · The sterically more demanding FGs ethylsulfonyl, ethoxysulfonyl, and diethoxyphosphonyl induced diastereofacial selectivity in favor of the corresponding syn products, with diethoxyphosphonyl being the most effective. The substrate with FG = PO(OEt)2 delivered, with eight different arenes, the corresponding syn substitution … WebMar 15, 2012 · High diastereofacial selectivity has also been achieved in the intermolecular Diels–Alder reaction. The chiral auxiliary approach has proved extremely effective < 91COS(5)315 >. The auxiliary can be attached to either the alkene (Equation (102)) or, less commonly, the diene (Equation (103)). Once again, the use of Lewis acid … terminal island fci address