供体-受体环丙烷与1,3-二烯的形式[3 + 2]环加成反应：环戊烷的组装
Formal [3 + 2]-Cycloaddition of Donor-Acceptor Cyclopropanes to 1,3-Dienes: Cyclopentane Assembly.
作者信息
Budynina Ekaterina M, Ivanova Olga A, Chagarovskiy Alexey O, Grishin Yuri K, Trushkov Igor V, Melnikov Mikhail Ya
机构信息
Department of Chemistry, M.V. Lomonosov Moscow State University , Leninskie Gory 1-3, Moscow 119991, Russia.
Federal Research Center of Pediatric Hematology, Oncology and Immunology named after Dmitrii Rogachev , Samory Mashela 1, Moscow 117997, Russia.
出版信息
J Org Chem. 2015 Dec 18;80(24):12212-23. doi: 10.1021/acs.joc.5b02146. Epub 2015 Dec 1.
We report a new simple method to access highly substituted cyclopentanes via Lewis acid-initiated formal [3 + 2]-cycloaddition of donor-acceptor cyclopropanes to 1,3-dienes. This process displays exceptional chemo- and regioselectivity as well as high diastereoselectivity, allowing for the synthesis of functionalized cyclopentanes and bicyclic cyclopentane-based structures in moderate to high yields. Moreover, one-pot synthesis of biologically relevant cyclopentafuranones, based on reaction of donor-acceptor cyclopropanes with dienes, has been developed.
我们报道了一种新的简便方法，可通过路易斯酸引发的给体-受体环丙烷与1,3-二烯的形式[3 + 2]环加成反应来制备高度取代的环戊烷。该过程具有出色的化学选择性和区域选择性以及高非对映选择性，能够以中等到高的产率合成官能化的环戊烷和基于双环环戊烷的结构。此外，基于给体-受体环丙烷与二烯的反应，已经开发出了与生物学相关的环戊呋喃酮的一锅法合成。
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