缩醛对空间调控的对映体纯N-亚磺酰基亚胺的立体选择性自由基加成反应。

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

作者信息

Akindele Tito, Yamada Ken-ichi, Sejima Takumi, Maekawa Masaru, Yamamoto Yasutomo, Nakano Mayu, Tomioka Kiyoshi

机构信息

Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.

出版信息

Chem Pharm Bull (Tokyo). 2010 Feb;58(2):265-9. doi: 10.1248/cpb.58.265.

DOI:10.1248/cpb.58.265

PMID:20118594

Abstract

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.

摘要

通过使用二甲基锌-空气和三氟化硼二乙醚，将缩醛自由基加成到对映体纯的N-亚磺酰基亚胺上，合成了对映体富集的磺酰胺。使用均三甲苯亚磺酰基可观察到更高水平的立体控制。此外，从磺酰胺产物可获得对映体纯度高的胺和氨基醇。