Azetidines and bisazetidines. Their synthesis and use as the key intermediates to enantiomerically pure diamines, amino alcohols, and polyamines

I Ojima, M Zhao, T Yamato, K Nakahashi…

Index: Ojima, Iwao; Zhao, Mangzhu; Yamato, Takehiko; Nakahashi, Kazuaki; Yamashita, Mitsuo; Abe, Rumiko Journal of Organic Chemistry, 1991 , vol. 56, # 18 p. 5263 - 5277

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Citation Number: 115

Abstract

Next, monochloroalane (AlH2Cl) and dichloroalane (AIHClz) were examined. We found that AlH2Cl and AlHC12 prepared in situ from LiAIHl and AlC13 in ether13 converted 1 into 2 in quite high yields (85-100%) without being accompanied by 3 (entries 8-23). Similarly, 3- azidoazetidin-2-ones (4) were converted to 3-aminoazetidines (5) in high yields (79- 100%)(eq 2). In these cases, the reduction of carbonyl and azide functionality proceeded ...