Microwave-assisted regioselective ring opening of non-activated aziridines by lithium aluminium hydride.
A new synthetic protocol for the LiAlH(4)-promoted reduction of non-activated aziridines under microwave conditions was developed. Thus, ring opening of 2-(acetoxymethyl)aziridines provided the corresponding beta-amino alcohols, which were then used as eligible substrates in the synthesis of 5-methylmorpholin-2-ones via condensation with glyoxal in THF. The same procedure was applied for the preparation of novel 5(R)- and 5(S)-methylmorpholin-2-ones starting from the corresponding enantiopure 2-(hydroxymethyl)aziridines. Additionally, 2-(methoxymethyl)- and 2-(phenoxymethyl)aziridines were treated with LiAlH(4) under microwave irradiation, giving rise to either isopropylamines or 1-methoxypropan-2-amines depending on the reaction conditions.
Stanković
Sonja
S
Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
D'hooghe
Matthias
M
De Kimpe
Norbert
N
D017607:Aluminum Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D000605:Amino Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D001388:Aziridines / Q000138:chemical synthesis / Q000737:chemistry*; D018020:Lithium Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D008872:Microwaves; D009025:Morpholines / Q000138:chemical synthesis / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D017607:Aluminum Compounds; D000605:Amino Alcohols; D001388:Aziridines; D018020:Lithium Compounds; D009025:Morpholines; C042073:lithium aluminum hydride