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烷氧基硼酸酯与过氧缩醛的动态动力学螺环化/氧杂-迈克尔加成串联反应：苯并稠合螺环缩酮的对映选择性和非对映选择性合成

Dynamic Kinetic Spiroketalization/Oxa-Michael Addition Cascade of Alkoxyboronates and Peroxyacetals: Enantio- and Diastereoselective Synthesis of Benzannulated Spiroketals.

作者信息

Midya Abhisek, Maity Sanjay, Ghorai Prasanta

机构信息

Department of Chemistry, Indian Institute of Science Education and Research (IISER) Bhopal, Bhopal By-pass Road, Bhauri, Bhopal, 462066, India.

出版信息

Chemistry. 2017 Aug 22;23(47):11216-11220. doi: 10.1002/chem.201701291. Epub 2017 Aug 3.

DOI:10.1002/chem.201701291
PMID:28640461
Abstract

A unified dynamic kinetic spiroketalization/enantioselective oxa-Michael addition cascade of an aromatic ketone tethered to an alkoxyboronate and an enone moiety has been developed using cinchona alkaloid based amino-thiourea/squaramide organocatalysts to provide isobenzofuran-based benzannulated spiroketals with high diastereoselectivities and excellent enantioselectivities. Further, a dynamic kinetic peroxy-hemiacetalization/dynamic kinetic spiroketalization/enantioselective oxa-Michael addition cascade of the above substrates provides the corresponding exo-peroxy-benzannulated spiroketals with outstanding enantio- and diastereoselectivities.

摘要

利用基于金鸡纳生物碱的氨基硫脲/方酰胺有机催化剂，开发了一种将芳族酮与烷氧基硼酸酯和烯酮部分相连的统一动态动力学螺环化/对映选择性氧杂-Michael加成串联反应，以提供具有高非对映选择性和优异对映选择性的异苯并呋喃基苯并稠合螺环酮。此外，上述底物的动态动力学过氧半缩醛化/动态动力学螺环化/对映选择性氧杂-Michael加成串联反应提供了具有出色对映和非对映选择性的相应外型过氧苯并稠合螺环酮。

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