Zurro Mercedes, Asmus Sören, Bamberger Julia, Beckendorf Stephan, García Mancheño Olga
Institute for Organic Chemistry, University of Regensburg, Universitätsstrasse 31, 93053, Regensburg, Germany.
Straubing Center of Science for Renewable Resources (WZS), Schulgasse 16, 94315, Straubing, Germany.
Chemistry. 2016 Mar 7;22(11):3785-93. doi: 10.1002/chem.201504094. Epub 2016 Jan 7.
Easily accessible and tunable chiral triazoles have been introduced as a novel class of C-H bond-based H-donors for anion-binding organocatalysis. They have proven to be effective catalysts for the dearomatization reaction of different N-heteroarenes. Although this dearomatization approach represents a powerful strategy to build chiral heterocycles, to date only a few catalytic methods to this end exist. In this work, the organocatalyzed enantioselective Reissert-type dearomatization of isoquinoline derivatives employing a number of structurally diverse chiral triazoles as anion-binding catalysts was realized. The here presented method was employed to synthesize a number of chiral 1,2-dihydroisoquinoline substrates with an enantioselectivity up to 86:14 e.r. Moreover, a thorough study of the determining parameters affecting the activity of this type of anion- binding catalysts was carried out.
易于获得且可调节的手性三唑已被引入作为一类新型的基于C-H键的氢供体，用于阴离子结合有机催化。它们已被证明是不同N-杂芳烃脱芳构化反应的有效催化剂。尽管这种脱芳构化方法是构建手性杂环的有力策略，但迄今为止，为此目的的催化方法只有少数几种。在这项工作中，实现了使用多种结构多样的手性三唑作为阴离子结合催化剂对异喹啉衍生物进行有机催化的对映选择性赖瑟特型脱芳构化反应。本文提出的方法用于合成了一些对映选择性高达86:14 e.r.的手性1,2-二氢异喹啉底物。此外，还对影响这类阴离子结合催化剂活性的决定性参数进行了深入研究。
