852402-28-9Relevant articles and documents
Diastereoselective conjugate addition/cyclization/bromination: Access to four stereocenters in a single step
Liao, Junzhuo,Drueckhammer, Dale G.
, p. 1776 - 1778 (2018)
A stereoselective tandem conjugate addition reaction with a chiral amine-derived nucleophile is reported in which the enolate intermediate is quenched with 1,2-dibromotetrachloroethane as a mild brominating reagent. X-ray analysis of a subsequent derivative was used to prove the configuration at each of the four newly formed stereocenters. The resulting α-bromoester underwent selective transesterification catalyzed by mild base to allow selective manipulation of the two ester groups of the product.
Copper-catalyzed asymmetric allylic alkylation of halocrotonates: Efficient synthesis of versatile chiral multifunctional building blocks
Den Hartog, Tim,Macia, Beatriz,Minnaard, Adriaan J.,Feringa, Ben L.
experimental part, p. 999 - 1013 (2010/08/07)
The highly enantioselective synthesis of amethyl-substituted esters is reported in up to 90% yield and up to 99% ee using copper-TaniaPhos as chiral catalyst. The transformation proved scalable to at least 6.6 mmol (1.7 g scale). The products of this transformation have been further elaborated to multifunctional building blocks with a single (branched esters and acids) or multiple stereogenic centers (vicinal dimethyl esters, as well as, hydroxy- or iodosubstituted lactones).
Synthesis and Structure-Activity Relationships of Naftifine-Related Allylamine Antimycotics
Stuetz, Anton,Georgopoulos, Apostolos,Granitzer, Waltraud,Petranyi, Gabor,Berney, Daniel
, p. 112 - 125 (2007/10/02)
Naftifine (1) is the first representative of the new antifungal allylamine derivatives.Its biological activity is strictly bound to specific structural requirements that are unrelated to those of known antifungals.A tertiary allylamine function seems to be a prerequisite for activity against fungi.By systematic variation of the individual structural elements in 1, detailed structure-activity relationships are defined in which the phenyl ring is the structural feature permitting the widest variations.Versatile synthetic routes to allylamine derivatives and comparative biological data are presented.