New chiral monophosphite ligands containing BINOL and/or H8-BINOL bearing adamantyl substituents: effect of ligand scaffold on the enantioselective 1,4-conjugate addition of diethylzinc to cyclic enones

doi:10.1016/S1872-2067(10)60164-7

Paper

New chiral monophosphite ligands containing BINOL and/or H8-BINOL bearing adamantyl substituents: effect of ligand scaffold on the enantioselective 1,4-conjugate addition of diethylzinc to cyclic enones

Published 2011 · B. Wan, Y. Fuk, Lai-lai Wang

Chinese Journal of Catalysis

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Abstract

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A partially hydrogenated 2,2′-(1,1′-binaphthyl)phosphite scaffold and an adamantyl moiety effectively improves enantioselectivity in diethylzinc addition to cyclic enones, reaching up to 79%

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

New chiral monophosphite ligands containing BINOL and/or H8-BINOL bearing adamantyl substituents: effect of ligand scaffold on the enantioselective 1,4-conjugate addition of diethylzinc to cyclic enones

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References

Recent advances in enantioselective copper-catalyzed 1,4-addition.

Enantioselective copper-catalyzed 1,4-addition of organometallic reagents to alpha,beta-unsaturated compounds has advanced significantly, with improvements in stereoselectivity, catalyst loading, ligand structure, and substrate scope.

Helical triskelion monophosphites as ligands in asymmetric catalysis.

Helical triskelion monophosphites show respectable enantioselectivity in asymmetric hydrogenation of prochiral homoallylic alcohols, compared to less sterically congested BINOL-derived phenyl analogues.

Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions.

Copper-catalyzed conjugate addition and allylic substitution reactions enable enantioselective synthesis of complex organic molecules.

Cu-catalyzed enantioselective conjugate addition of diethylzinc to cyclic enones with chiral phosphite ligands derived from 1,2:5,6-di-O-cyclohexylidene-d-mannitol

Copper-catalyzed enantioselective conjugate addition of diethylzinc to cyclic enones with chiral phosphite ligands derived from 1,2:5,6-di-O-cyclohexylidene-

Sugar–phosphite–oxazoline and phosphite–phosphoroamidite ligand libraries for Cu-catalyzed asymmetric 1,4-addition reactions

Sugar-phosphite-oxazoline and phosphite-phosphoroamidite ligand libraries show good activity and enantioselectivity in Cu-catalyzed asymmetric 1,4-addition reactions, with enantioselectivity up

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