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Synthesis of N-protected 3,3-difluoroazetidin-2-ones

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Lacroix, Simon [UCL] Cheguillaume, A Gerard, Sabine [UCL] Marchand-Brynaert, Jacqueline [UCL]

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).

Document type Article de périodique (Journal article) – Article de recherche
Publication date 2003
Language Anglais
Journal information "Synthesis : journal of synthetic organic chemistry" - , no. 16, p. 2483-2486 (2003)
Peer reviewed yes
Publisher Georg Thieme Verlag Kg (Stuttgart)
issn 0039-7881
e-issn 1437-210X
Publication status Publié
Affiliations UCL - SC/CHIM - Département de chimie
UCL - FSA/AUCE - Département d'architecture, d'urbanisme et de génie civil environnemental
Keywords fluoroazetidinone ; Reformatsky-type reaction ; cycloaddition ; cyclization
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Bibliographic reference Lacroix, Simon ; Cheguillaume, A ; Gerard, Sabine ; Marchand-Brynaert, Jacqueline. Synthesis of N-protected 3,3-difluoroazetidin-2-ones. In: Synthesis : journal of synthetic organic chemistry, , no. 16, p. 2483-2486 (2003)
Permanent URL http://hdl.handle.net/2078.1/40639