Stereoselective synthesis of trans- and cis-2-aryl-3-(hydroxymethyl)aziridines through transformation of 4-aryl-3-chloro-beta-lactams and study of their ring opening.
trans- and cis-1-Alkyl-4-aryl-3-chloroazetidin-2-ones, prepared through cyclocondensation of chloroketene and the appropriate imines in a diastereoselective way, were transformed into the corresponding non-activated trans- and cis-2-aryl-3-(hydroxymethyl)aziridines via reductive ring contraction using LiAlH(4) in Et(2)O. Furthermore, trans-2-aryl-3-(hydroxymethyl)aziridines were transformed into 2-amino-3-arylpropan-1-ols and anti-2-amino-3-aryl-3-methoxypropan-1-ols by means of an unprecedented ring opening by LiAlH(4) and by MeOH, respectively. cis-2-Aryl-3-(hydroxymethyl)aziridines were shown to be highly reluctant to undergo ring opening by LiAlH(4) and MeOH under similar reaction conditions.
D'hooghe
Matthias
M
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, B-9000 Ghent, Belgium.
Mollet
Karen
K
Dekeukeleire
Stijn
S
De Kimpe
Norbert
N
D017607:Aluminum Compounds / Q000737:chemistry; D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry*; D007769:Lactams / Q000737:chemistry*; D018020:Lithium Compounds / Q000737:chemistry; D000432:Methanol / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
D017607:Aluminum Compounds; D001388:Aziridines; D007769:Lactams; D018020:Lithium Compounds; C042073:lithium aluminum hydride; D000432:Methanol