Facile access to a heterocyclic, sp3-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, sp³-rich chemical scaffold via a tandem condensation/intramolecular nitrone–alkene [3+2] cycloaddition strategy†

M. J. Rawling,^a T. E. Storr,^a W. A. Bawazir,^ab S. J. Cully,^a W. Lewis,^a M. S. I. T. Makki,^b I. R. Strutt,^c G. Jones,^c D. Hamza^c and R. A. Stockman*^a

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^a School of Chemistry, University of Nottingham, Nottingham, NG7 2RD, UK
E-mail: robert.stockman@nottingham.ac.uk
Fax: +44 (0)115 951356

^b Department of Chemistry, Faculty of Science, King Abdul-Aziz University, P.O. Box 80203, Jeddah 21315, Saudi Arabia

^c Sygnature Discovery Limited, BioCity, Pennyfoot Street, Nottingham, NG7 1GF, UK

Abstract

A heterocyclic, sp³-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.

Chemical Communications

Facile access to a heterocyclic, sp³-rich chemical scaffold via a tandem condensation/intramolecular nitrone–alkene [3+2] cycloaddition strategy†

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Facile access to a heterocyclic, sp³-rich chemical scaffold via a tandem condensation/intramolecular nitrone–alkene [3+2] cycloaddition strategy

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