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Catalytic Enantioselective aza-Reformatsky Reaction with Seven‐Membered Cyclic Imines Dibenzo[b,f][1,4]oxazepines

Abstract

A catalytic enantioselective aza-Reformatsky reaction is reported with cyclic dibenzo[b,f][1,4]oxazepines and ethyl iodoacetate leading to the synthesis of chiral ethyl 2-(10,11-dihydrodibenzo[b,f][1,4]oxazepin-11-yl)acetate derivatives with excellent yields and high enantioselectivities (up to 98% yield and 97:3 er) using a readily available diaryl prolinol L4 as chiral ligand and Me2Zn as zinc source in the presence of air atmosphere. Furthermore, different transformations were carried out with the corresponding chiral β-amino esters, preserving in all cases the optical purity.

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Publication details

The article was received on 26 Apr 2017, accepted on 17 May 2017 and first published on 18 May 2017


Article type: Research Article
DOI: 10.1039/C7QO00329C
Citation: Org. Chem. Front., 2017, Accepted Manuscript
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    Catalytic Enantioselective aza-Reformatsky Reaction with Seven‐Membered Cyclic Imines Dibenzo[b,f][1,4]oxazepines

    L. DeMunck, V. Sukowski, C. Vila, M. C. Muñoz and J. R. Pedro, Org. Chem. Front., 2017, Accepted Manuscript , DOI: 10.1039/C7QO00329C

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