Stereoselective synthesis of trans- and cis-2-aryl-3-(hydroxymethyl)aziridines through transformation of 4-aryl-3-chloro-β-lactams and study of their ring opening
作者： Matthias D'hooghe , Karen Mollet , Stijn Dekeukeleire , Norbert De Kimpe
DOI: 10.1039/B919864D
关键词:
摘要: trans- and cis-1-Alkyl-4-aryl-3-chloroazetidin-2-ones, prepared through cyclocondensation of chloroketene the appropriate imines in a diastereoselective way, were transformed into corresponding non-activated cis-2-aryl-3-(hydroxymethyl)aziridines via reductive ring contraction using LiAlH4 Et2O. Furthermore, trans-2-aryl-3-(hydroxymethyl)aziridines 2-amino-3-arylpropan-1-ols anti-2-amino-3-aryl-3-methoxypropan-1-ols by means an unprecedented opening MeOH, respectively. cis-2-Aryl-3-(hydroxymethyl)aziridines shown to be highly reluctant undergo MeOH under similar reaction conditions.
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