Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, B-9000 Ghent, Belgium.
Org Biomol Chem. 2010 Feb 7;8(3):607-15. doi: 10.1039/b919864d. Epub 2009 Dec 4.
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.
反式和顺式 1-烷基-4-芳基-3-氯氮杂环丁-2-酮，通过氯代亚酮与适当的亚胺的立体选择性环缩合制备，然后通过 LiAlH(4)在 Et(2)O 中还原环缩合，转化为相应的非活化的反式和顺式 2-芳基-3-(羟甲基)氮杂环丁烷。此外，反式 2-芳基-3-(羟甲基)氮杂环丁烷通过 LiAlH(4)进行前所未有的开环，分别转化为 2-氨基-3-芳基-1-丙醇和反式-2-氨基-3-芳基-3-甲氧基-1-丙醇。顺式 2-芳基-3-(羟甲基)氮杂环丁烷在类似的反应条件下，通过 LiAlH(4)和 MeOH 开环时，表现出高度的不情愿。
