Expedient and modular access to 2-azabicyclic architectures by iron-catalyzed dehydrative coupling of alcohol-bearing allylic lactams

Katie Hovenkotter; Hannah Braunstein; Spencer Langevin; Timothy K Beng

doi:10.1039/c6ob02652d

Expedient and modular access to 2-azabicyclic architectures by iron-catalyzed dehydrative coupling of alcohol-bearing allylic lactams

Org Biomol Chem. 2017 Feb 1;15(5):1217-1221. doi: 10.1039/c6ob02652d.

Authors

Katie Hovenkotter¹, Hannah Braunstein¹, Spencer Langevin¹, Timothy K Beng¹

Affiliation

¹ Department of Chemistry, Central Washington University, Ellensburg, WA 98926, USA. TimothyB@cwu.edu.

PMID: 28090613
DOI: 10.1039/c6ob02652d

Abstract

A high-yielding, cost-effective, modular and environmentally benign approach to [5,5]- or [6,5]-2-azabicyclic architectures bearing vicinal stereocenters, by Fe-catalyzed intramolecular dehydrative coupling of readily affordable alcohol-bearing allylic lactams is presented.

MeSH terms

Alcohols / chemistry*
Architecture*
Aza Compounds / chemical synthesis*
Aza Compounds / chemistry
Bridged Bicyclo Compounds / chemical synthesis*
Bridged Bicyclo Compounds / chemistry
Catalysis
Dehydration
Iron / chemistry*
Lactams / chemistry*
Molecular Structure
Stereoisomerism

Substances

Alcohols
Aza Compounds
Bridged Bicyclo Compounds
Lactams
Iron