Asymmetric synthesis of 5-(1-hydroxyalkyl)tetrazoles by catalytic enantioselective Passerini-type reactions

• Published in: Angewandte Chemie, International Edition, vol. 47, num. 49, p. 9454-9457
• Publication date: 2008

Three-component Passerini reactions (P-3CR) of a wide range of aldehydes and isocyanides, with hydrazoic acid in toluene, in the presence of a [(salen)-AlMe]-complex catalyst afford 5-(1-hydroxyalkyl)tetrazoles in good-to-excellent yields and enantiomeric excess. A tandem Michael addn./enantioselective P-3CR, using an acrolein substrate, affords highly functionalized tetrazoles. [on SciFinder (R)]

Keywords: Addition reaction catalysts (Passerini; asym. synthesis of 5-(1-hydroxyalkyl)tetrazoles by catalytic enantioselective three-component Passerini-type reactions of aldehydes and isocyanides with hydrazoic acid in the presence of a [(salen)-AlMe]-complex catalyst); Passerini reaction; Stereoselective synthesis (asym. synthesis of 5-(1-hydroxyalkyl)tetrazoles by catalytic enantioselective three-component Passerini-type reactions of aldehydes and isocyanides with hydrazoic acid); Aldehydes; Isocyanides Role: RCT (Reactant) ; RACT (Reactant or reagent) (asym. synthesis of 5-(1-hydroxyalkyl)tetrazoles by catalytic enantioselective three-component Passerini-type reactions of aldehydes and isocyanides with hydrazoic acid); Michael reaction (catalytic enantioselective tandem Michael addn./three-component Passerini-type reactions of acrolein and isocyanides with hydrazoic acid); Michael reaction catalysts (catalytic enantioselective tandem Michael addn./three-component Passerini-type reactions of acrolein and isocyanides with hydrazoic acid in the presence of a [(salen)-AlMe]-complex catalyst) ; asym synthesis hydroxyalkyltetrazole; tetrazole hydroxyalkyl asym synthesis; aluminum salen catalyst enantioselective three component Passerini reaction; enantioselective three component Passerini reaction aldehyde isocyanide hydrazoic acid; Michael addn Passerini reaction tandem aluminum salen catalyst

Note:

CAN 150:214285

28-10

Heterocyclic Compounds (More Than One Hetero Atom)

National 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.

78-84-2 (Isobutanal); 104-53-0 (3-Phenylpropanal); 111-71-7 (Heptanal); 122-78-1 (Phenylacetaldehyde); 123-38-6 (Propanal); 590-86-3; 931-53-3 (Isocyanocyclohexane); 931-54-4 (Phenyl isocyanide); 1802-16-0 (3-Pyridinepropanal); 1930-94-5; 2043-61-0 (Cyclohexanecarboxaldehyde); 2769-71-3 (2,6-Dimethylphenyl isocyanide); 3966-32-3 ((R)-O-Methylmandelic acid); 7050-85-3 (4-Dimethylaminophenyl isocyanide); 7175-47-5 (4-Methylphenyl isocyanide); 10340-91-7; 10349-38-9; 20600-54-8 (3-Methylphenyl isocyanide); 26164-26-1; 33554-73-3 (4-Bromophenyl isocyanide); 39687-95-1; 165459-70-1 Role: RCT (Reactant), RACT (Reactant or reagent) (asym. synthesis of 5-(1-hydroxyalkyl)tetrazoles by catalytic enantioselective three-component Passerini-type reactions of aldehydes and isocyanides with hydrazoic acid); 1111754-91-6P; 1111755-14-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (asym. synthesis of 5-(1-hydroxyalkyl)tetrazoles by catalytic enantioselective three-component Passerini-type reactions of aldehydes and isocyanides with hydrazoic acid); 7782-79-8 (Hydrazoic acid) Role: RGT (Reagent), RACT (Reactant or reagent) (asym. synthesis of 5-(1-hydroxyalkyl)tetrazoles by catalytic enantioselective three-component Passerini-type reactions of aldehydes and isocyanides with hydrazoic acid); 1111754-93-8P; 1111754-94-9P; 1111754-95-0P; 1111754-96-1P; 1111754-97-2P; 1111754-98-3P; 1111755-00-0P; 1111755-01-1P; 1111755-02-2P; 1111755-03-3P; 1111755-05-5P; 1111755-06-6P; 1111755-07-7P; 1111755-08-8P; 1111755-09-9P; 1111755-10-2P; 1111755-12-4P; 1111755-13-5P; 1111755-15-7P; 1111755-20-4P; 1111755-21-5P; 1111755-22-6P Role: SPN (Synthetic preparation), PREP (Preparation) (asym. synthesis of 5-(1-hydroxyalkyl)tetrazoles by catalytic enantioselective three-component Passerini-type reactions of aldehydes and isocyanides with hydrazoic acid); 250611-18-8P Role: SPN (Synthetic preparation), PREP (Preparation) (asym. synthesis of 5-(1-hydroxyalkyl)tetrazoles by catalytic enantioselective three-component Passerini-type reactions of aldehydes and isocyanides with hydrazoic acid in the presence of a [(salen)-AlMe]-complex catalyst); 107-02-8 (Acrolein) Role: RCT (Reactant), RACT (Reactant or reagent) (catalytic enantioselective tandem Michael addn./three-component Passerini-type reactions of acrolein and isocyanides with hydrazoic acid); 1111755-16-8P; 1111755-18-0P; 1111755-19-1P Role: SPN (Synthetic preparation), PREP (Preparation) (catalytic enantioselective tandem Michael addn./three-component Passerini-type reactions of acrolein and isocyanides with hydrazoic acid)

Reference

• EPFL-ARTICLE-158057
• doi:10.1002/anie.200804213

Record created on 2010-11-25, modified on 2017-05-12