107243-99-2Relevant articles and documents
C(10)-substituted camphors and fenchones by electrophilic treatment of 2-methylenenorbornan-1-ols: Enantiospecificity, scope, and limitations
De la Moya Cerero, Santiago,Martinez, Antonio Garcia,Vilar, Enrique Teso,Fraile, Amelia Garcia,Maroto, Beatriz Lora
, p. 1451 - 1458 (2003)
Valuable chiral sources of C(10)-substituted camphors and C(10)-substituted fenchones can be straightforwardly obtained by treatment of an appropriate, easily obtainable, camphor- or fenchonederived 2-methylenenorbornan-1-ol with an electrophilic reagent. The process takes place via a tandem regioselective carbon-carbon double-bond addition/stereocontrolled Wagner-Meerwein rearrangement. A complete study of the enantiospecificity, scope, and limitations of this process, as well as about the role played by the hydroxyl group attached at the C(1) bridgehead position of the starting 2-methylenenorbornan-1-ols, has been realized. The feasibility of the described methodology has been exemplified by the highly efficient enantiospecific preparation of several interesting C(10)-halogen-, C(10)-O-, C(10)-S-, C(10)-Se-, or C(10)-C-substituted camphors and fenchones.
A new straightforward preparation of enantiopure 10-hydroxycamphor
Garcia Martinez, Antonio,Teso Vilar, Enrique,Garcia Fraile, Amelia,De La Moya Cerero, Santiago,Lora Maroto, Beatriz
, p. 4437 - 4440 (2000)
The enantiospecific preparation of the interesting chiral source 10-hydroxycamphor from commercially available camphor is described. The synthetic procedure takes place straightforwardly in only three synthetic steps with a high overall yield. The key step of the described route is based on the ability of a 2-methylenenorbornane intermediate to undergo an enantiospecific Wagner-Meerwein rearrangement under electrophilic treatment with m-CPBA.
Straightforward synthesis of poly(dimethylsiloxane) phases with immobilized (1R)-3-(perfluoroalkanoyl)camphorate metal complexes and their application in enantioselective complexation gas chromatography
Spallek, Markus J.,Storch, Golo,Trapp, Oliver
, p. 3929 - 3945 (2012)
A straightforward synthesis of novel chiral polysiloxane-based metal stationary phases immobilized through a propylenoxy linker (Chirasil-Metal- OC3) to the polymeric backbone is presented. Synthesis was accomplished in six steps with high overall yields starting from commercially available, enantiopure (+)-(1S)-camphorsulfonic acid. Two different approaches towards Chirasil-Metal phases featuring either a propylenoxy or propylenthio linker used for immobilization through hydrosilylation are presented. Furthermore, a new protocol for the fluoroacylation, which is one of the key steps in the synthesis of (1R)-3-(perfluoroalkanoyl)camphorate metal complexes, was developed to improve the isolation and overall yield. The immobilization of (1R,4S)-10-(allyloxy)-3-(heptafluorobutanoyl)camphor -10-(allyloxy)-hfbc -onto polysiloxanes as well as the incorporation of nickel(II), oxovanadium(IV), europium(III), and lanthanum(III) was characterized by FT ATR IR and NMR spectroscopy. Overall, seven different Chirasil-Metal-OC3 polymers with different separation properties were prepared by metal incorporation and variation of the amount of immobilized (1R,4S)-10-(allyloxy)-3- (heptafluorobutanoyl)camphor (10-allyloxy-hfbc: 3.5, 10.2, and 20.0 %). Their performance in enantioselective complexation gas chromatography was systematically studied and excellent enantioselectivity was found for Chirasil-Nickel-OC3. Separation of 29 small-sized compounds, encompassing, among others, epoxides, substituted alkenes and alkynes as well as alcohols and amides, was achieved with high separation factors α. The synthetic strategy, enantiomer separations and thermal stability (up to 160 °C) demonstrates the versatility of the newly derived Chirasil-Metal-OC 3 phases.
Enantioselective addition of organozinc reagents to carbonyl compounds catalyzed by a camphor derived chiral γ-amino thiol ligand
Wu, Hsyueh-Liang,Wu, Ping-Yu,Cheng, Ying-Ni,Uang, Biing-Jiun
, p. 2656 - 2665 (2016/05/10)
In this article, the design and synthesis of the chiral camphor derived γ-amino thiol ligand 17 and its application in catalytic enantioselective carbon-carbon forming reactions through the addition of organozinc reagents to carbonyl compounds is described. The catalytic activity and enantioselectivity of ligand 17 is demonstrated in the enantioselective addition of various organozinc reagents to aldehydes and ketoesters, offering the corresponding alcohols in high yields and enantioselectivities. The role of the mercapto group in the highly enantioselective 1,2-addition reaction of organozincs to aldehyde is also discussed.
