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Merck
  • Stereoselective radical addition of an acetal to sterically tuned enantiomerically pure N-sulfinyl imines.

Stereoselective radical addition of an acetal to sterically tuned enantiomerically pure N-sulfinyl imines.

Chemical & pharmaceutical bulletin (2010-02-02)
Tito Akindele, Ken-ichi Yamada, Takumi Sejima, Masaru Maekawa, Yasutomo Yamamoto, Mayu Nakano, Kiyoshi Tomioka
摘要

Enantiomerically enriched sulfonamides were synthesized by the radical addition of an acetal to enantiomerically pure N-sulfinyl imines using dimethylzinc-air and boron trifluoride diethyl etherate. Higher levels of stereocontrol were observed by using a mesitylenesulfinyl group. Furthermore, an amine and an amino alcohol with high enantiomeric purity were obtainable from the sulfonamide product.

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Sigma-Aldrich
三氟化硼二乙醚, for synthesis
Sigma-Aldrich
三氟化硼二乙醚, purified by redistillation, ≥46.5% BF3 basis