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Synthesis 2003(16): 2483-2486
DOI: 10.1055/s-2003-42415
DOI: 10.1055/s-2003-42415
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of N-Protected 3,3-Difluoroazetidin-2-ones
Further Information
Received
21 July 2003
Publication Date:
29 September 2003 (online)
Publication History
Publication Date:
29 September 2003 (online)
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Abstract
Representative N-protected 3,3-difluoroazetidin-2-ones 3 were obtained, either in one step by cycloaddition of zinc enolate 1 derived from ethyl bromodifluoroacetate onto N,N′,N′′-trisubstituted hexahydro-1,3,5-triazines 2 (Schiff base trimer) in the case of 3a [N-(p-methoxybenzyl) derivative], or in two steps consisting of a Reformatsky-type reaction for the preparation of N-substituted 3-amino-2,2-difluoropropanotes 8 followed by N1-C2 cyclization under basic conditions in the cases of 3b (N-anisyl derivative) and 3c (N-benzhydryl derivative).
Key words
fluoroazetidinone - Reformatsky-type reaction - cycloaddition - cyclization
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