Facile access to a heterocyclic, sp(3)-rich chemical scaffold via a tandem condensation/intramolecular nitrone-alkene [3+2] cycloaddition strategy

M J Rawling; T E Storr; W A Bawazir; S J Cully; W Lewis; M S I T Makki; I R Strutt; G Jones; D Hamza; R A Stockman

doi:10.1039/c5cc05070g

Facile access to a heterocyclic, sp(3)-rich chemical scaffold via a tandem condensation/intramolecular nitrone-alkene [3+2] cycloaddition strategy

Chem Commun (Camb). 2015 Aug 18;51(64):12867-70. doi: 10.1039/c5cc05070g.

Authors

M J Rawling¹, T E Storr, W A Bawazir, S J Cully, W Lewis, M S I T Makki, I R Strutt, G Jones, D Hamza, R A Stockman

Affiliation

¹ School of Chemistry, University of Nottingham, Nottingham, NG7 2RD, UK. robert.stockman@nottingham.ac.uk.

PMID: 26169627
DOI: 10.1039/c5cc05070g

Abstract

A heterocyclic, sp(3)-rich chemical scaffold was synthesised in just 6 steps via a highly regio- and diastereo-selective tandem nitrone formation/intramolecular nitrone-alkene [3+2] cycloaddition reaction. A library of 543 lead-like compounds based on the scaffold core has been produced.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkenes / chemistry*
Cycloaddition Reaction
Heterocyclic Compounds / chemistry*
Nitrogen Oxides / chemistry*

Substances

Alkenes
Heterocyclic Compounds
Nitrogen Oxides
nitrones