Catalytic Asymmetric Passerini-Type Reaction: Chiral Aluminum-Organophosphate-Catalyzed Enantioselective alpha -Addition of Isocyanides to Aldehydes

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)]


Published in:
Journal of Organic Chemistry, 74, 21, 8396-8399
Year:
2009
Keywords:
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
0022-3263
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:




 Record created 2010-11-25, last modified 2018-09-13


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