1355509-79-3Relevant academic research and scientific papers
Enantioselective functionalization of allylic C-H bonds following a strategy of functionalization and diversification
Sharma, Ankit,Hartwig, John F.
, p. 17983 - 17989 (2014/01/06)
We report the enantioselective functionalization of allylic C-H bonds in terminal alkenes by a strategy involving the installation of a temporary functional group at the terminal carbon atom by C-H bond functionalization, followed by the catalytic diversification of this intermediate with a broad scope of reagents. The method consists of a one-pot sequence of palladium-catalyzed allylic C-H bond oxidation under neutral conditions to form linear allyl benzoates, followed by iridium-catalyzed allylic substitution. This overall transformation forms a variety of chiral products containing a new C-N, C-O, C-S, or C-C bond at the allylic position in good yield with a high branched-to-linear selectivity and excellent enantioselectivity (ee ≤97%). The broad scope of the overall process results from separating the oxidation and functionalization steps; by doing so, the scope of nucleophile encompasses those sensitive to direct oxidative functionalization. The high enantioselectivity of the overall process is achieved by developing an allylic oxidation that occurs without acid to form the linear isomer with high selectivity. These allylic functionalization processes are amenable to an iterative sequence leading to (1,n)-functionalized products with catalyst-controlled diastereo- and enantioselectivity. The utility of the method in the synthesis of biologically active molecules has been demonstrated.
A flexible organocatalytic enantioselective synthesis of heptadeca-1-ene-4,6-diyne-3S,8R,9S,10S-tetrol and its congeners
Kumaraswamy, Gullapalli,Sadaiah, Kadivendi
, p. 262 - 271 (2012/01/14)
A unified enantioselective route is developed for the synthesis of heptadeca-1-ene-4,6-diyne-3S,8R,9S,10S-tetrol and its synthetic congeners. A proline-catalyzed aminoxylation, cross-metathesis, Wittig reaction, and catalytic dihydroxylation are key steps
The use of COP-OAc in the catalyst-controlled syntheses of 1,3-polyols
Kirsch, Stefan F.,Klahn, Philipp,Menz, Helge
supporting information; experimental part, p. 3592 - 3603 (2011/12/21)
An iterative strategy to the 1,3-polyol motif is described. The use of the catalytic asymmetric Overman esterification for the construction of all stereogenic centers is broadly examined as are the sequences to extend the developing polyol chain. The iterative strategies are applied to the total syntheses of rugulactone and polyrhacitides A and B. 1 Introduction 2 Results and Discussion 2.1 Chain Elongation via RCM (Cycle A) 2.2 Total Synthesis of Rugulactone 2.3 Chain Elongation via Ando Olefination (Cycle B) and Total Syntheses of Polyrhacitides A and B 2.4 Useful Variants 3 Conclusions. Georg Thieme Verlag Stuttgart. New York.
