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

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

Yue, Tao
•
Wang, Mei-Xiang
•
Wang, De-Xian
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2008
Angewandte Chemie International Edition

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)]

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Type
research article
DOI
10.1002/anie.200804213
Author(s)
Yue, Tao
Wang, Mei-Xiang
Wang, De-Xian
Zhu, Jieping  
Date Issued

2008

Publisher

Wiley-VCH Verlag GmbH

Published in
Angewandte Chemie International Edition
Volume

47

Issue

49

Start page

9454

End page

9457

Subjects

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

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)

Editorial or Peer reviewed

REVIEWED

Written at

OTHER

EPFL units
LSPN  
Available on Infoscience
November 25, 2010
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/58409
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