Catalytic Asymmetric Passerini-Type Reaction: Chiral Aluminum-Organophosphate-Catalyzed Enantioselective alpha -Addition of Isocyanides to Aldehydes
2009
Abstract
A chiral Lewis acid catalyst was prepd. by mixing 2 equiv of chiral binol-derived organophosphoric acid and 1 equiv of Et2AlCl. In the presence of a catalytic amt. of [I]2Al(III)Cl complex (0.05 equiv), reaction between alpha -isocyanoacetamides and aldehydes afforded the corresponding 5-aminooxazoles, e.g. II, in good yields and enantioselectivities. Complex [I]2Al(III)Cl isolated as a white solid displayed similar reactivity as that prepd. in situ. [on SciFinder (R)]
Details
Title
Catalytic Asymmetric Passerini-Type Reaction: Chiral Aluminum-Organophosphate-Catalyzed Enantioselective alpha -Addition of Isocyanides to Aldehydes
Author(s)
Yue, Tao ; Wang, Mei-Xiang ; Wang, De-Xian ; Masson, Geraldine ; Zhu, Jieping
Published in
Journal of Organic Chemistry
Volume
74
Issue
21
Pages
8396-8399
Date
2009
ISSN
0022-3263
Keywords
Aldehydes; Isocyanides Role: RCT (Reactant); RACT (Reactant or reagent) (stereoselective prepn. of aminooxazoles via Al-organophosphate-catalyzed asym. Passerini-type reaction of alpha -isocyanatoacetamides and aldehydes); Passerini reaction; Passerini reaction catalysts (stereoselective; stereoselective prepn. of aminooxazoles via Al-organophosphate-catalyzed asym. Passerini-type reaction of alpha -isocyanatoacetamides and aldehydes); organophosphate aluminum catalyst isocyanoacetamide aldehyde asym Passerini type reaction; aminooxazole stereoselective prepn
Note
CAN 151:508512
28-6
Heterocyclic Compounds (More Than One Hetero Atom)
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry,Chinese Academy of Sciences,Beijing,Peop. Rep. China.
Journal
written in English.
96-10-6 (Diethylaluminum chloride); 922711-71-5 Role: CAT (Catalyst use), USES (Uses) (stereoselective prepn. of aminooxazoles via Al-organophosphate-catalyzed asym. Passerini-type reaction of alpha -isocyanatoacetamides and aldehydes); 1192888-03-1P Role: CAT (Catalyst use), SPN (Synthetic preparation), PREP (Preparation), USES (Uses) (stereoselective prepn. of aminooxazoles via Al-organophosphate-catalyzed asym. Passerini-type reaction of alpha -isocyanatoacetamides and aldehydes); 78-84-2 (Isobutanal); 111-71-7 (Heptanal); 122-78-1 (Phenylacetaldehyde); 123-38-6 (Propanal); 85059-38-7; 85059-48-9; 215648-69-4; 336105-88-5; 911817-35-1; 943030-28-2 Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselective prepn. of aminooxazoles via Al-organophosphate-catalyzed asym. Passerini-type reaction of alpha -isocyanatoacetamides and aldehydes); 951241-53-5P; 951241-54-6P; 951241-55-7P; 1192583-11-1P; 1192583-12-2P; 1192583-13-3P; 1192583-14-4P; 1192583-15-5P; 1192583-16-6P; 1192583-17-7P; 1192583-18-8P; 1192583-19-9P Role: SPN (Synthetic preparation), PREP (Preparation) (stereoselective prepn. of aminooxazoles via Al-organophosphate-catalyzed asym. Passerini-type reaction of alpha -isocyanatoacetamides and aldehydes)
28-6
Heterocyclic Compounds (More Than One Hetero Atom)
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry,Chinese Academy of Sciences,Beijing,Peop. Rep. China.
Journal
written in English.
96-10-6 (Diethylaluminum chloride); 922711-71-5 Role: CAT (Catalyst use), USES (Uses) (stereoselective prepn. of aminooxazoles via Al-organophosphate-catalyzed asym. Passerini-type reaction of alpha -isocyanatoacetamides and aldehydes); 1192888-03-1P Role: CAT (Catalyst use), SPN (Synthetic preparation), PREP (Preparation), USES (Uses) (stereoselective prepn. of aminooxazoles via Al-organophosphate-catalyzed asym. Passerini-type reaction of alpha -isocyanatoacetamides and aldehydes); 78-84-2 (Isobutanal); 111-71-7 (Heptanal); 122-78-1 (Phenylacetaldehyde); 123-38-6 (Propanal); 85059-38-7; 85059-48-9; 215648-69-4; 336105-88-5; 911817-35-1; 943030-28-2 Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselective prepn. of aminooxazoles via Al-organophosphate-catalyzed asym. Passerini-type reaction of alpha -isocyanatoacetamides and aldehydes); 951241-53-5P; 951241-54-6P; 951241-55-7P; 1192583-11-1P; 1192583-12-2P; 1192583-13-3P; 1192583-14-4P; 1192583-15-5P; 1192583-16-6P; 1192583-17-7P; 1192583-18-8P; 1192583-19-9P Role: SPN (Synthetic preparation), PREP (Preparation) (stereoselective prepn. of aminooxazoles via Al-organophosphate-catalyzed asym. Passerini-type reaction of alpha -isocyanatoacetamides and aldehydes)
Laboratories
LSPN
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Record creation date
2010-11-25