Issue 37, 2016
From the journal:

Organic & Biomolecular Chemistry

Modular access to vicinally functionalized allylic (thio)morpholinonates and piperidinonates by substrate-controlled annulation of 1,3-azadienes with hexacyclic anhydrides†‡

Hannah Braunstein,a   Spencer Langevin,a   Monique Khim,a   Jonathan Adamson,a   Katie Hovenkotter,a   Lindsey Kotlarz,a   Brandon Manskera  and  Timothy K. Beng*a  

* Corresponding authors

a Department of Chemistry, Central Washington University, Ellensburg, WA 98926, USA
E-mail: TimothyB@cwu.edu

Abstract

A modular substrate-controlled hexannulation of inherently promiscuous 1,3-azadienes with hexacyclic anhydrides, which affords versatile vicinally functionalized allylic lactams, in high yields, regio- and stereoselectivities is described.

Graphical abstract: Modular access to vicinally functionalized allylic (thio)morpholinonates and piperidinonates by substrate-controlled annulation of 1,3-azadienes with hexacyclic anhydrides

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Article information

DOI
https://doi.org/10.1039/C6OB01526C
Article type
Paper
Submitted
18 Jul 2016
Accepted
30 Aug 2016
First published
05 Sep 2016

Org. Biomol. Chem., 2016,14, 8864-8872

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Modular access to vicinally functionalized allylic (thio)morpholinonates and piperidinonates by substrate-controlled annulation of 1,3-azadienes with hexacyclic anhydrides

H. Braunstein, S. Langevin, M. Khim, J. Adamson, K. Hovenkotter, L. Kotlarz, B. Mansker and T. K. Beng, Org. Biomol. Chem., 2016, 14, 8864 DOI: 10.1039/C6OB01526C

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