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Paper | Special issue | Vol 99, No. 2, 2019, pp.919-941
Published online, 5th December, 2018
DOI: 10.3987/COM-18-S(F)59
Rapid Stereoselective Syntheses of Heteroarene-Fused Azacycles via Diastereoselective Conjugate Addition of Heteroaryl Substituted Lithium Amides

Stephen G. Davies,* Ai M. Fletcher, Katherine E. Holder, Paul M. Roberts, James E. Thomson, and David Zimmer

*Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, U.K.


Conjugate addition of heteroaryl substituted lithium amides to a range of α,β-unsaturated esters followed by in situ enolate oxidation with (–)-(camphorsulfonyl)oxaziridine gave the corresponding α-hydroxy-β-amino esters. Subsequent Friedel-Crafts type cyclisation of these α-hydroxy-β-amino esters gave a range of heteroarene-fused azacycles in good yields and high diastereoselectivities.