Bronsted Acid Catalyzed Enantioselective Three-Component Reaction Involving the alpha Addition of Isocyanides to Imines

That a chiral phosphoric acid is able to catalyze the three-component reaction of aldehydes, anilines, and alpha -isocyanoacetamides, leading to 2-(1-aminoalkyl)-5-aminooxazoles in excellent yields and moderate to good enantioselectivities, was reported. [on SciFinder (R)]


Published in:
Angewandte Chemie, International Edition, 48, 36, 6717-6721, S6717/1-S6717/100
Year:
2009
Keywords:
Isocyanides Role: RCT (Reactant) ; RACT (Reactant or reagent) (aminocarbonylmethyl; stereoselective prepn. of 2-(1-aminoalkyl)-5-aminooxazoles via chiral phosphoric acid catalyzed three-component reaction of aldehydes ; anilines ; and alpha -isocyanoacetamides); Amines Role: RCT (Reactant) ; RACT (Reactant or reagent) (aryl; stereoselective prepn. of 2-(1-aminoalkyl)-5-aminooxazoles via chiral phosphoric acid catalyzed three-component reaction of aldehydes ; anilines ; and alpha -isocyanoacetamides); Bronsted acids Role: CAT (Catalyst use) ; SPN (Synthetic preparation) ; PREP (Preparation) ; USES (Uses) (binaphthalenyl; stereoselective prepn. of 2-(1-aminoalkyl)-5-aminooxazoles via chiral phosphoric acid catalyzed three-component reaction of aldehydes ; anilines ; and alpha -isocyanoacetamides); Heterocyclic compounds Role: SPN (Synthetic preparation) ; PREP (Preparation) (nitrogen-oxygen; stereoselective prepn. of 2-(1-aminoalkyl)-5-aminooxazoles via chiral phosphoric acid catalyzed three-component reaction of aldehydes ; anilines ; and alpha -isocyanoacetamides); Heterocyclization; Heterocyclization catalysts; Stereoselective synthesis (stereoselective prepn. of 2-(1-aminoalkyl)-5-aminooxazoles via chiral phosphoric acid catalyzed three-component reaction of aldehydes ; anilines ; and alpha -isocyanoacetamides); Aldehydes; Imines Role: RCT (Reactant) ; RACT (Reactant or reagent) (stereoselective prepn. of 2-(1-aminoalkyl)-5-aminooxazoles via chiral phosphoric acid catalyzed three-component reaction of aldehydes ; anilines ; and alpha -isocyanoacetamides); Multicomponent reaction (three-component; stereoselective prepn. of 2-(1-aminoalkyl)-5-aminooxazoles via chiral phosphoric acid catalyzed three-component reaction of aldehydes ; anilines ; and alpha -isocyanoacetamides); Amides Role: RCT (Reactant) ; RACT (Reactant or reagent) (alpha -isocyano; stereoselective prepn. of 2-(1-aminoalkyl)-5-aminooxazoles via chiral phosphoric acid catalyzed three-component reaction of aldehydes ; anilines ; and alpha -isocyanoacetamides) ; aldehyde aniline isocyanoacetamide imine chiral phosphoric acid enantioselective heterocyclization; aminoalkyl aminooxazole stereoselective prepn; enantioselective three component heterocyclization catalyst chiral phosphoric acid
Note:
CAN 151:491023
28-6
Heterocyclic Compounds (More Than One Hetero Atom)
National Natural Laboratory for Molecular Sciences, Laboratory of Chemical Biology, Institute of Chemistry,Chinese Academy of Sciences,Beijing,Peop. Rep. China.
Journal
1433-7851
written in English.
695162-87-9 Role: CAT (Catalyst use), USES (Uses) (stereoselective prepn. of 2-(1-aminoalkyl)-5-aminooxazoles via chiral phosphoric acid catalyzed three-component reaction of aldehydes, anilines, and alpha -isocyanoacetamides); 1041186-20-2P; 1192413-02-7P; 1192413-04-9P Role: CAT (Catalyst use), SPN (Synthetic preparation), PREP (Preparation), USES (Uses) (stereoselective prepn. of 2-(1-aminoalkyl)-5-aminooxazoles via chiral phosphoric acid catalyzed three-component reaction of aldehydes, anilines, and alpha -isocyanoacetamides); 1192413-05-0 Role: FMU (Formation, unclassified), RCT (Reactant), FORM (Formation, nonpreparative), RACT (Reactant or reagent) (stereoselective prepn. of 2-(1-aminoalkyl)-5-aminooxazoles via chiral phosphoric acid catalyzed three-component reaction of aldehydes, anilines, and alpha -isocyanoacetamides); 78-84-2; 95-55-6; 104-94-9; 106-40-1; 106-47-8; 111-71-7 (Heptanal); 371-40-4; 455-14-1; 630-19-3; 2043-61-0 (Cyclohexanecarboxaldehyde); 18169-40-9; 56414-96-1; 62965-35-9; 67434-29-1; 85059-38-7; 85059-48-9; 123534-00-9; 336105-88-5; 500555-97-5; 845791-23-3; 911817-35-1; 943030-28-2; 1192278-33-3; 1236962-07-4; 1236962-26-7; 1236962-34-7; 1236962-43-8; 1236962-50-7; 1236962-58-5; 1236962-65-4 Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselective prepn. of 2-(1-aminoalkyl)-5-aminooxazoles via chiral phosphoric acid catalyzed three-component reaction of aldehydes, anilines, and alpha -isocyanoacetamides); 1192277-68-1P; 1192278-27-5P; 1192278-29-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (stereoselective prepn. of 2-(1-aminoalkyl)-5-aminooxazoles via chiral phosphoric acid catalyzed three-component reaction of aldehydes, anilines, and alpha -isocyanoacetamides); 1192277-59-0P; 1192277-62-5P; 1192277-65-8P; 1192277-71-6P; 1192277-74-9P; 1192277-77-2P; 1192277-80-7P; 1192277-82-9P; 1192277-85-2P; 1192277-88-5P; 1192277-91-0P; 1192277-94-3P; 1192277-96-5P; 1192277-99-8P; 1192278-00-4P; 1192278-03-7P; 1192278-06-0P; 1192278-08-2P; 1192278-11-7P; 1192278-13-9P; 1192278-15-1P; 1192278-17-3P; 1192278-19-5P; 1192278-22-0P; 1192278-23-1P; 1192278-25-3P; 1192278-34-4P; 1192278-35-5P; 1192278-36-6P; 1192278-37-7P; 1192278-38-8P; 1192278-39-9P; 1192278-40-2P; 1192278-41-3P; 1192278-42-4P; 1192278-43-5P; 1192278-44-6P; 1192278-45-7P; 1192278-46-8P; 1192278-47-9P; 1192278-48-0P; 1192278-49-1P; 1192278-50-4P; 1192278-51-5P; 1192278-52-6P; 1192278-53-7P; 1192278-54-8P; 1192278-55-9P; 1192278-56-0P; 1192278-57-1P; 1192278-58-2P; 1192278-59-3P; 1192413-03-8P Role: SPN (Synthetic preparation), PREP (Preparation) (stereoselective prepn. of 2-(1-aminoalkyl)-5-aminooxazoles via chiral phosphoric acid catalyzed three-component reaction of aldehydes, anilines, and alpha -isocyanoacetamides)
Laboratories:




 Record created 2010-11-25, last modified 2018-12-03


Rate this document:

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