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

2012; Wiley; Volume: 51; Issue: 15 Linguagem: Inglês

10.1002/anie.201109061

1521-3773

Carmen Simal, Tomáš Lébl, Alexandra M. Z. Slawin, Andrew D. Smith,

Synthesis and Catalytic Reactions

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. Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.