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Journal article

Phosphoramidite ligands in iridium-catalyzed allylic substitution

A new phosphoramidite ligand was used in the iridium-catalyzed allylic substitution reaction. This permitted high regio- and enantioselectivity on a wide variety of substrates and nucleophiles. Because of the stereospecificity of the reaction obtained by using branched substrates, a kinetic resoln. reaction was attempted. The origin of the impressive efficiency of this ligand in terms of kinetics was explored in detail, as was the role of the substituent in the ortho-position of the amine moiety. [on SciFinder (R)]

    Keywords: Amination kinetics (iridium-catalyzed stereoselective allylic amination reaction using phosphoramidite derivs. as ligands); Density functional theory (iridium-catalyzed stereoselective allylic substitution reaction using chiral N ; N-[(aryl)ethyl]dinaphtho[2 ; 1-d:1' ; 2'-f][1 ; 3 ; 2]dioxaphosphepin-4-amine (phosphoramidite) ligand and related study of d. functional theory model); Amination (regioselective; iridium-catalyzed stereoselective allylic amination reaction using phosphoramidite derivs. as ligands); Amination; Amination catalysts (stereoselective; iridium-catalyzed stereoselective allylic amination reaction using phosphoramidite derivs. as ligands) ; iridium stereoselective allylic substitution phosphoramidite ligand; allylic substitution asym catalysis chiral ligand iridium phosphoramidite

    Note:

    CAN 145:145318

    25-7

    Benzene, Its Derivatives, and Condensed Benzenoid Compounds

    Department of Organic Chemistry,University of Geneva,Geneva,Switz.

    Journal

    0947-6539

    written in English.

    40032-55-1P; 86386-72-3P; 897963-63-2P Role: BYP (Byproduct), PREP (Preparation) (iridium-catalyzed stereoselective allylic amination reaction using phosphoramidite derivs. as ligands); 100-46-9 (Benzyl amine); 107-11-9 (Allylamine) Role: RCT (Reactant), RACT (Reactant or reagent) (iridium-catalyzed stereoselective allylic amination reaction using phosphoramidite derivs. as ligands); 111-26-2P (n-Hexylamine); 104937-80-6P; 223384-31-4P; 244221-60-1P; 735334-59-5P Role: SPN (Synthetic preparation), PREP (Preparation) (iridium-catalyzed stereoselective allylic amination reaction using phosphoramidite derivs. as ligands); 776316-53-1 Role: CAT (Catalyst use), USES (Uses) (iridium-catalyzed stereoselective allylic substitution reaction using chiral N,N-[(aryl)ethyl]dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine (phosphoramidite) derivs. as ligands); 209482-27-9P ((11bS)-N,N-Bis[(1S)-1-phenylethyl]dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine); 342813-26-7P; 776316-48-4P; 850796-15-5P; 850796-17-7P; 850797-26-1P; 898262-64-1P; 898262-65-2P Role: CAT (Catalyst use), SPN (Synthetic preparation), PREP (Preparation), USES (Uses) (iridium-catalyzed stereoselective allylic substitution reaction using chiral N,N-[(aryl)ethyl]dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine (phosphoramidite) derivs. as ligands); 850796-16-6P Role: CAT (Catalyst use), PRP (Properties), SPN (Synthetic preparation), PREP (Preparation), USES (Uses) (iridium-catalyzed stereoselective allylic substitution reaction using chiral N,N-[(aryl)ethyl]dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine (phosphoramidite) ligand and related study of d. functional theory model); 81586-82-5P; 119793-72-5P; 496789-07-2P; 685139-88-2P; 897963-53-0P Role: BYP (Byproduct), PREP (Preparation) (iridium-catalyzed stereoselective allylic substitution reaction using chiral phosphoramidite derivs. as ligands); 886759-00-8 Role: CAT (Catalyst use), USES (Uses) (iridium-catalyzed stereoselective allylic substitution reaction using chiral phosphoramidite derivs. as ligands); 105-45-3; 609-02-9; 2049-80-1; 2497-18-9; 7217-71-2 (alpha-Ethenylbenzenemethanol acetate); 18424-76-5; 21040-45-9; 41302-34-5; 85217-69-2; 107574-36-7; 170938-16-6; 373362-32-4; 496789-05-0; 496789-06-1; 512789-12-7; 897963-49-4; 897963-50-7; 897963-51-8 Role: RCT (Reactant), RACT (Reactant or reagent) (iridium-catalyzed stereoselective allylic substitution reaction using chiral phosphoramidite derivs. as ligands); 897963-57-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (iridium-catalyzed stereoselective allylic substitution reaction using chiral phosphoramidite derivs. as ligands); 92747-24-5P; 129101-14-0P; 164527-50-8P; 164713-27-3P; 189884-47-7P; 189884-50-2P; 776296-25-4P; 776296-26-5P; 776296-27-6P; 776296-28-7P; 776296-29-8P; 897963-54-1P; 897963-55-2P; 898262-66-3P Role: SPN (Synthetic preparation), PREP (Preparation) (iridium-catalyzed stereoselective allylic substitution reaction using chiral phosphoramidite derivs. as ligands); 12112-67-3 (Di-micro -chlorobis[(1,2,5,6-eta)-1,5-cyclooctadiene]diiridium) Role: CAT (Catalyst use), USES (Uses) (iridium-catalyzed stereoselective allylic substitution reaction using phosphoramidite derivs. as ligands); 73930-97-9 Role: RCT (Reactant), RACT (Reactant or reagent) (iridium-catalyzed stereoselective allylic substitution reaction using phosphoramidite derivs. as ligands); 87751-69-7P; 96482-64-3P Role: SPN (Synthetic preparation), PREP (Preparation) (iridium-catalyzed stereoselective allylic substitution reaction using phosphoramidite derivs. as ligands); 865-34-9 (Lithium methoxide) Role: RGT (Reagent), RACT (Reactant or reagent) (lithium methoxide as additive in iridium-catalyzed stereoselective allylic substitution reaction using phosphoramidite derivs. as ligands); 811803-79-9P; 897963-59-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of (phenyl)-3-cyclopentene-1,1-dicarboxylic acid di Et ester and related kinetic resoln. study); 98-86-2 (Acetophenone); 100-06-1 (1-(4-Methoxyphenyl)ethanone); 577-16-2 (1-(2-Methylphenyl)ethanone); 579-74-8 (1-(2-Methoxyphenyl)ethanone); 941-98-0 (1-(1-Naphthalenyl)ethanone); 2627-86-3; 5379-16-8; 10420-89-0; 18531-99-2 ((S)-BINOL); 20050-17-3; 41851-59-6; 68285-24-5; 76279-30-6 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of chiral N,N-[(aryl)ethyl]dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine (phosphoramidite) derivs.); 90933-74-7P; 222180-06-5P; 676567-87-6P; 850790-52-2P; 850790-53-3P; 850790-54-4P; 897963-64-3P; 897963-65-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of chiral N,N-[(aryl)ethyl]dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine (phosphoramidite) derivs.); 129646-79-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of alpha-(ethenyl)benzenemethanol acetate)

    Reference

    Record created on 2007-10-22, modified on 2016-08-08

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