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)]


Published in:
Chemistry - A European Journal, 12, 13, 3596-3609
Year:
2006
Keywords:
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)
Laboratories:




 Record created 2007-10-22, last modified 2018-03-17


Rate this document:

Rate this document:
1
2
3
 
(Not yet reviewed)