Issue 30, 2012

Enantioselective synthesis of 2,5-dihydrobenzo[b]azepine derivatives via iridium-catalyzed asymmetric allylic amination with 2-allylanilines and ring-closing-metathesis reaction

Abstract

Iridium-catalyzed asymmetric allylic amination of allylic carbonates with 2-allylanilines was realized. With a catalyst generated from 2 mol% of [Ir(dbcot)Cl]2 (dbcot = dibenzo[a,e]cyclooctatetraene) and 4 mol% of phosphoramidite ligand (L3), the amination products were obtained in up to 99% yield and 99% ee. Subjecting amination products to trifluoroacetyl protection and ring-closing-metathesis reaction provided an efficient synthesis of enantioenriched 2,5-dihydrobenzo[b]azepine derivatives.

Graphical abstract: Enantioselective synthesis of 2,5-dihydrobenzo[b]azepine derivatives via iridium-catalyzed asymmetric allylic amination with 2-allylanilines and ring-closing-metathesis reaction

Supplementary files

Article information

Article type
Paper
Submitted
05 जनवरी 2012
Accepted
02 मार्च 2012
First published
02 मार्च 2012

Org. Biomol. Chem., 2012,10, 5932-5939

Enantioselective synthesis of 2,5-dihydrobenzo[b]azepine derivatives via iridium-catalyzed asymmetric allylic amination with 2-allylanilines and ring-closing-metathesis reaction

K. Ye, L. Dai and S. You, Org. Biomol. Chem., 2012, 10, 5932 DOI: 10.1039/C2OB00036A

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