对映选择性氮杂-Sakurai 环化反应：硫脲作为氢键供体和路易斯碱的双重作用。
Enantioselective Aza-Sakurai Cyclizations: Dual Role of Thiourea as H-Bond Donor and Lewis Base.
机构信息
Department of Chemistry and Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States.
出版信息
J Am Chem Soc. 2016 Nov 16;138(45):14848-14851. doi: 10.1021/jacs.6b09736. Epub 2016 Nov 3.
Abstract
An enantioselective, catalytic aza-Sakurai cyclization of chlorolactams has been developed as an efficient entry into indolizidine and quinolizidine frameworks. Structure-enantioselectivity relationship studies and mechanistic analysis point to a dual role of the catalyst wherein the thiourea moiety of the catalyst is engaged in both anion binding and Lewis base activation of a substrate.
摘要
已开发出一种对映选择性、催化的氮杂-Sakurai 环化反应，用于氯代内酰胺，这是进入吲哚嗪和喹诺嗪骨架的有效方法。结构-对映选择性关系研究和机理分析表明催化剂具有双重作用，其中催化剂的硫脲部分既参与了阴离子结合，又激活了底物的路易斯碱。
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