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Dihydropyridones: Catalytic Asymmetric Synthesis, N- to C-Sulfonyl Transfer, and Derivatizations

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  • The authors thank the Royal Society (A.D.S.) and the EU (IEF for C.S.) for funding, and the EPSRC Mass Spectrometry Service Centre.

Abstract

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Benzotetramisole (1) promotes the reaction of ammonium enolates derived from arylacetic acids with N-tosyl-α,β-unsaturated ketimines, thus giving dihydropyridones with high diastereo- and enantiocontrol (see scheme). These products readily undergo N- to C-sulfonyl photoisomerization and are derivatized to afford stereodefined piperidines and tetrahydropyrans.

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