Abstract
Two different synthetic pathways are presented that provide access to enantiopure sulfinyl hydrazones; in both addition of sulfenic acid/unsaturation represents the crucial step of the procedure. The obtained results are discussed in terms of regioselectivity in the formation of α- and/or β-sulfinyl α,β-unsaturated products when sulfenic acids are reacted with substrates showing carbonyl conjugated triple bonds, and/or their derivatives. Despite its structural limitations, (R
S ,E,E )-2-[(1S )-isoborneol-10-sulfinyl]-2-butenal dimethylhydrazone (6 ) behaves as 1-azabuta-1,3-diene in hetero Diels-Alder reaction with N -methylmaleimide, giving a unique cycloadduct with complete endo and facial selectivities.
Key words
1-aza-1,3-dienes - chiral auxiliaries - stereoselective synthesis - sulfenic acids - sulfoxides
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