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Diastereoselective synthesis of 2-fluoroaziridine-2-carboxylates by Reformatsky-type aza-Darzens reaction

✍ Scribed by Atsushi Tarui; Naoto Kawashima; Kazuyuki Sato; Masaaki Omote; Akira Ando

Book ID: 104097953
Publisher: Elsevier Science
Year: 2010
Tongue: French
Weight: 262 KB
Volume: 51
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2010.06.030

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✦ Synopsis

The reaction of ethyl dibromofluoroacetate with imines using zinc metal gave 2-fluoroaziridine-2-carboxylates via aza-Darzens reaction of the primary product of the Reformatsky reaction with high diastereoselectivity in excellent yields (quantitative yield and Dr = 85:15). This chemoselective formation of 2-fluoroaziridines was achieved by using CH 3 CN as a solvent. Interestingly, the reaction proceeded without activation of zinc metal, which was necessary for the Reformatsky reaction of bromodifluoroacetate.

None of a-bromo-a-fluoro-b-lactams, four-membered cyclization products, and noncyclized 3-amino-2bromo-2-fluorocarboxylic esters, usual Reformatsky adducts, were formed.

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