The Experts below are selected from a list of 351 Experts worldwide ranked by ideXlab platform
Kellie L Tuck - One of the best experts on this subject based on the ideXlab platform.
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an asymmetric synthesis of grandisol a constituent of the aggregation pheromone of the cotton boll weevil via a kinetic resolution
Journal of Organic Chemistry, 2000Co-Authors: David P G Hamon, Kellie L TuckAbstract:A novel approach to the asymmetric synthesis of (+)-grandisol, (1R, 2S)-isopropenyl-1-methylcyclobutaneethanol, involves the use of catalytic kinetic resolution of a Primary Allylic Alcohol, [(1RS, 5SR)-5-methylbicyclo[3.2.0]hept-2-en-2-yl] methanol. The Allylic Alcohol is prepared in four steps from simple achiral materials involving the use of a modified Shapiro reaction. The resolved Alcohol (95% ee) is then reduced in two steps to the corresponding methyl alkene, (1S,5R)-2,5-dimethylbicyclo[3.2.0]hept-2-ene. This alkene is converted to (+)-grandisol (95% ee), in three steps, by modified literature procedures.
David P G Hamon - One of the best experts on this subject based on the ideXlab platform.
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an asymmetric synthesis of grandisol a constituent of the aggregation pheromone of the cotton boll weevil via a kinetic resolution
Journal of Organic Chemistry, 2000Co-Authors: David P G Hamon, Kellie L TuckAbstract:A novel approach to the asymmetric synthesis of (+)-grandisol, (1R, 2S)-isopropenyl-1-methylcyclobutaneethanol, involves the use of catalytic kinetic resolution of a Primary Allylic Alcohol, [(1RS, 5SR)-5-methylbicyclo[3.2.0]hept-2-en-2-yl] methanol. The Allylic Alcohol is prepared in four steps from simple achiral materials involving the use of a modified Shapiro reaction. The resolved Alcohol (95% ee) is then reduced in two steps to the corresponding methyl alkene, (1S,5R)-2,5-dimethylbicyclo[3.2.0]hept-2-ene. This alkene is converted to (+)-grandisol (95% ee), in three steps, by modified literature procedures.
Tuck, Kellie Louise - One of the best experts on this subject based on the ideXlab platform.
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A New Asymmetric Synthesis of (+) Grandisol via a Kinetic Resoltuion
'Elsevier BV', 1999Co-Authors: Hamon, David P. G., Tuck, Kellie LouiseAbstract:Available online 28 October 1999.A novel approach to the asymmetric synthesis of (+)-grandisol involves the use of catalytic kinetic resolution of a Primary Allylic Alcohol. The Allylic Alcohol is prepared in 4 steps from simple achiral materials and the resolved Alcohol (95%e.e.) is reduced in 2 steps to the corresponding methyl alkene. This alkene is converted to (+)-grandisol (95%e.e.).David P.G. Hamon and Kellie L. Tuc
Kleczka Margarethe - One of the best experts on this subject based on the ideXlab platform.
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Strong Asymmetry in the Perepoxide Bifurcation Mechanism: The Large-Group Effect in the Singlet Oxygen Ene Reaction with Allylic Alcohols
'Wiley', 2017Co-Authors: Griesbeck, Axel G., Goldfuss Bernd, Jaeger Christina, Bruellingen Eric, Lippold Tim, Kleczka MargaretheAbstract:The singlet oxygen reactions of sterically crowded Allylic Alcohols result in the preferential formation of g-hydroperoxy Alcohols with regioselectivities up to 98:2. The kinetic cis effect still prevails in the first, rate-determining step of this two-step non-intermediate ene mechanism (k(E-5)/k(Z-5)=1.9). The Primary Allylic Alcohol 3 showed no regioselectivity at all, increasing the steric demands at the a carbon and directing the singlet oxygen addition towards the gamma carbon up to 98:2 regioselectivity. DFT calculations rationalized these results and show the decisive role of the symmetry-breaking bifurcation following the early transition states. The use of the products as substrates for the synthesis of five-and seven-membered ring peroxides, namely 4-methylene-1,2-dioxolanes and 6-methylene-1,2,4-trioxepanes, by rare earth metal complexes as Lewis acids is also demonstrated
Hamon, David P. G. - One of the best experts on this subject based on the ideXlab platform.
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A New Asymmetric Synthesis of (+) Grandisol via a Kinetic Resoltuion
'Elsevier BV', 1999Co-Authors: Hamon, David P. G., Tuck, Kellie LouiseAbstract:Available online 28 October 1999.A novel approach to the asymmetric synthesis of (+)-grandisol involves the use of catalytic kinetic resolution of a Primary Allylic Alcohol. The Allylic Alcohol is prepared in 4 steps from simple achiral materials and the resolved Alcohol (95%e.e.) is reduced in 2 steps to the corresponding methyl alkene. This alkene is converted to (+)-grandisol (95%e.e.).David P.G. Hamon and Kellie L. Tuc