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Molecules 2017, 22(11), 1871; doi:10.3390/molecules22111871

Synthesis of Substituted Oxo-Azepines by Regio- and Diastereoselective Hydroxylation

Department of Molecular Sciences, Macquarie University, Sydney, NSW 2109, Australia
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Author to whom correspondence should be addressed.
Received: 27 September 2017 / Revised: 26 October 2017 / Accepted: 27 October 2017 / Published: 31 October 2017
(This article belongs to the Section Organic Synthesis)
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Abstract

Substituted seven-membered N-heterocycles are prevalent bioactive epitopes and useful synthons for preparing enzyme inhibitors or molecular recognition systems. To fully exploit the chemical properties of this flexible N-heterocycle scaffold, efficient methods for its diverse functionalization are required. Here we utilize the late-stage oxidation of tetrahydroazepines as an approach to access densely functionalized oxo-azepines in a total of 8 steps and ~30% overall yield from commercially available starting materials. Hydroboration of tetrahydroazepines proceeded with diastereoselectivity in a substrate-dependent manner to yield regioisomeric azepanols before their oxidation to the corresponding oxo-azepines. Regioselectivity of the hydroboration step may be improved moderately by a rhodium catalyst, albeit with loss of conversion to a competing hydrogenation pathway. Overall our method allows efficient access to azepanols and oxo-azepines as versatile epitopes and synthons with a high degree of diastereoselectivity and moderate regioselectivity. View Full-Text
Keywords: azepines; hydroboration; diastereoselectivity; oxo-azepines; DFT azepines; hydroboration; diastereoselectivity; oxo-azepines; DFT
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Spedding, H.; Karuso, P.; Liu, F. Synthesis of Substituted Oxo-Azepines by Regio- and Diastereoselective Hydroxylation. Molecules 2017, 22, 1871.

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