期刊
TETRAHEDRON
卷 65, 期 35, 页码 7277-7288出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.01.110
关键词
Host-guest; Chiral photochemistry; Electrocyclization; Pyridones; Confined space; Supramolecular assemblies
资金
- National Science Foundation, USA [CHE-0213042, CHE-0531802]
- National Institute of Health [RO1 GM074031]
Chiral induction during the photoelectrocyclization of pyridones included within octa acid (C)A) capsule has been established. Chiral induction is brought about by a chiral auxiliary appended to the reactive pyridone moiety. Importantly, the same chiral auxiliary while ineffective in acetonitrile solution is found to be effective within the confined space of OA capsule. The diastereomeric excess of 92% obtained here is comparable only to that in solid state. OA capsule, we believe, provides restriction to the rotational motions of the reactant pyridone and chiral auxiliary and thus places the chiral auxiliary in a selective conformation with respect to the reactive pyridone part. A correlation between the position of the methyl group on the pyridone ring and diastereoselectivity was noted. Structures of the host-guest complexes were examined by H-1 NMR and the data were used to obtain preliminary information concerning the mechanism of chiral induction within the confined spaces of OA capsule. (C) 2009 Elsevier Ltd. All rights reserved.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据