research article

Chiral Salen-Aluminum Complex as a Catalyst for Enantioselective alpha -Addition of Isocyanides to Aldehydes: Asymmetric Synthesis of 2-(1-Hydroxyalkyl)-5-aminooxazoles

Wang, Shi-Xin
•
Wang, Mei-Xiang
•
Wang, De-Xian
Show more
2007
Organic Letters

In the presence of a catalytic amt. of (Schiff base)Al(III)Cl complex (Schiff base of (R,R)-1,2-cyclohexanediamine with 3,5-di-tert-butyl-2-hydroxybenzaldehyde), reaction between alpha -isocyanoacetamides and aldehydes afforded the corresponding 5-aminooxazoles in good yields and enantioselectivity, e.g. 76 % (80 %ee) (S)-1-[4-benzyl-5-(morpholin-4-yl)oxazol-2-yl]-2-methyl-1-propanol from 2-isocyano-1-(morpholin-4-yl)-3-phenyl-1-propanone and isobutanal. [on SciFinder (R)]

Type
research article
DOI
10.1021/ol7014658
Author(s)
Wang, Shi-Xin
•
Wang, Mei-Xiang
•
Wang, De-Xian
•
Zhu, Jieping  
Date Issued

2007

Published in
Organic Letters
Volume

9

Issue

18

Start page

3615

End page

3618

Subjects

Isocyanides Role: RCT (Reactant)

•

RACT (Reactant or reagent) (carbamoyl; chiral salen-aluminum complex as catalyst for enantioselective alpha -addn. of isocyanides to aldehydes providing 2-(1-hydroxyalkyl)-5-aminooxazoles); Stereoselective synthesis (chiral salen-aluminum complex as catalyst for enantioselective alpha -addn. of isocyanides to aldehydes providing 2-(1-hydroxyalkyl)-5-aminooxazoles); Aldehydes Role: RCT (Reactant)

•

RACT (Reactant or reagent) (chiral salen-aluminum complex as catalyst for enantioselective alpha -addn. of isocyanides to aldehydes providing 2-(1-hydroxyalkyl)-5-aminooxazoles); Addition reaction; Addition reaction catalysts (stereoselective; chiral salen-aluminum complex as catalyst for enantioselective alpha -addn. of isocyanides to aldehydes providing 2-(1-hydroxyalkyl)-5-aminooxazoles); Amides Role: RCT (Reactant)

•

RACT (Reactant or reagent) (alpha -isocyano; chiral salen-aluminum complex as catalyst for enantioselective alpha -addn. of isocyanides to aldehydes providing 2-(1-hydroxyalkyl)-5-aminooxazoles)

•

Schiff aluminum catalysis asym addn isocyanide aldehyde aminohydroxyalkyloxazole synthesis; oxazole amino hydroxyalkyl asym synthesis aluminum Schiff complex catalysis

Note

CAN 147:406723

28-6

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.

7772-99-8 (Stannous chloride); 753001-91-1 Role: CAT (Catalyst use), USES (Uses) (catalyst comparison; chiral salen-aluminum complex as catalyst for enantioselective alpha -addn. of isocyanides to aldehydes providing 2-(1-hydroxyalkyl)-5-aminooxazoles); 78-84-2 (Isobutanal); 100-52-7 (Benzaldehyde); 104-88-1 (4-Chlorobenzaldehyde); 122-78-1 (Phenylacetaldehyde); 123-38-6 (Propanal); 135-02-4 (2-Methoxybenzaldehyde); 555-16-8 (4-Nitrobenzaldehyde); 630-19-3 (Pivalaldehyde); 2043-61-0 (Cyclohexanecarboxaldehyde); 3132-99-8 (3-Bromobenzaldehyde); 17407-55-5 ((2S)-2-Hydroxy-3-methylbutanoic acid); 56414-96-1 (2-Amino-1-(morpholino)ethanone); 60656-87-3 (2-(Benzyloxy)acetaldehyde); 67434-29-1 (2-Isocyano-1-(morpholin-4-yl)ethanone); 85059-48-9 (DL-2-Isocyano-1-(morpholin-4-yl)-3-phenyl-1-propanone); 500555-97-5 (N,N-Diethyl-2-isocyano-3-phenylpropanamide); 845791-23-3 (L-2-Isocyano-1-(morpholin-4-yl)-3-phenyl-1-propanone) Role: RCT (Reactant), RACT (Reactant or reagent) (chiral salen-aluminum complex as catalyst for enantioselective alpha -addn. of isocyanides to aldehydes providing 2-(1-hydroxyalkyl)-5-aminooxazoles); 951241-52-4P ((2S)-2-Hydroxy-3-methyl-N-[2-(morpholino)-2-oxoethyl]butanamide); 951241-53-5P ((S)-1-[4-Benzyl-5-(morpholin-4-yl)oxazol-2-yl]-2-methyl-1-propanol); 951241-54-6P ((S)-1-[4-Benzyl-5-(morpholin-4-yl)oxazol-2-yl]-1-propanol); 951241-55-7P ((S)-1-[4-Benzyl-5-(morpholin-4-yl)oxazol-2-yl]-2-phenylethanol); 951241-56-8P ((S)-4-Benzyl-5-(morpholin-4-yl)oxazol-2-ylmethanol); 951241-57-9P ((S)-1-[4-Benzyl-5-(morpholin-4-yl)oxazol-2-yl]-2,2-dimethyl-1-propanol); 951241-58-0P ((S)-1-[4-Benzyl-5-(morpholin-4-yl)oxazol-2-yl]-2-(benzyloxy)ethanol); 951241-59-1P ((S)-4-Benzyl-5-(morpholin-4-yl)oxazol-2-ylmethanol); 951241-60-4P ((S)-4-Benzyl-5-(morpholin-4-yl)oxazol-2-ylmethanol); 951241-61-5P ((S)-4-Benzyl-5-(morpholin-4-yl)oxazol-2-ylmethanol); 951241-62-6P ((S)-4-Benzyl-5-(morpholin-4-yl)oxazol-2-ylmethanol); 951241-63-7P ((S)-1-[4-Benzyl-5-(diethylamino)oxazol-2-yl]-2-methyl-1-propanol); 951241-64-8P ((S)-4-Benzyl-5-(diethylamino)oxazol-2-ylmethanol) Role: SPN (Synthetic preparation), PREP (Preparation) (chiral salen-aluminum complex as catalyst for enantioselective alpha -addn. of isocyanides to aldehydes providing 2-(1-hydroxyalkyl)-5-aminooxazoles); 96-10-6 (Chlorodiethylaluminum); 18531-94-7 ((R)-Binol); 20989-17-7 ((S)-2-Amino-2-phenylethanol); 62086-04-8; 128249-70-7 (2,6-Bis((4R)-4,5-dihydro-4-phenyloxazol-2-yl)pyridine) Role: CAT (Catalyst use), USES (Uses) (cocatalyst comparison; chiral salen-aluminum complex as catalyst for enantioselective alpha -addn. of isocyanides to aldehydes providing 2-(1-hydroxyalkyl)-5-aminooxazoles); 951241-65-9P ((S)-2-Methyl-1-[5-(morpholin-4-yl)oxazol-2-yl]-1-propanol) Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (hydrolysis; chiral salen-aluminum complex as catalyst for enantioselective alpha -addn. of isocyanides to aldehydes providing 2-(1-hydroxyalkyl)-5-aminooxazoles); 250611-13-3 Role: CAT (Catalyst use), USES (Uses) (preferred catalyst; chiral salen-aluminum complex as catalyst for enantioselective alpha -addn. of isocyanides to aldehydes providing 2-(1-hydroxyalkyl)-5-aminooxazoles)

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/20.500.14299/58425