Rapid stereoselective syntheses of heteroarene-fused azacycles via diastereoselective conjugate addition of heteroaryl substituted lithium amidest
Davies SG., Fletcher AM., Holder KE., Roberts PM., Thomson JE., Zimmer D.
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.