吡啶鎓盐阳离子-π络合物的面选择性加成：手性1,4-二氢吡啶的合成
Face-selective addition to a cation-pi complex of a pyridinium salt: synthesis of chiral 1,4-dihydropyridines.
作者信息
Yamada Shinji, Morita Chisako
机构信息
Department of Chemistry, Faculty of Science, Ochanomizu University, Bunkyo-ku, Tokyo 112-8610, Japan.
出版信息
J Am Chem Soc. 2002 Jul 17;124(28):8184-5. doi: 10.1021/ja0203317.
PMID:12105887
Abstract
Selective shielding of one side of the pyridinium face by way of intramolecular cation-pi complex formation enabled nucleophiles to attack only from the non-shielded side, and consequently, chiral 1,4-dihydropyridines were produced stereoselectively with up to 99% de. The structure of the cation-pi complex was elucidated by 1H NMR studies and X-ray analysis.
摘要
通过分子内阳离子-π络合物的形成对吡啶鎓面的一侧进行选择性屏蔽，使得亲核试剂只能从未屏蔽的一侧进攻，因此，能够立体选择性地生成手性1,4-二氢吡啶，非对映体过量最高可达99%。通过1H NMR研究和X射线分析阐明了阳离子-π络合物的结构。
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