Directed Arylation of 7‐Oxabicyclo[2.2.1]heptane to Prepare 3D Fragments

Author:

Caplin Max J.1ORCID,Alderson Imogen M.1,Foley Daniel J.1ORCID

Affiliation:

1. School of Physical and Chemical Sciences University of Canterbury Christchurch 8041 New Zealand

Abstract

AbstractDirected Pd‐catalysed β‐(hetero)arylation of the 7‐oxabicyclo[2.2.1]heptane framework is described. Arylated products were formed in up to 99 % yield, and heteroarylated products in up to 88 % yield with complete diastereoselectivity. Different minor diarylated side products were formed, depending on whether electron deficient aryl or pyridyl iodides were used as the coupling partners. Cleavage of the 8‐aminoquinoline directing group provided small bridged compounds that may be of value in fragment based drug discovery.

Funder

University of Canterbury

Royal Society of Chemistry

Publisher

Wiley

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