通过 1,3-二氮杂环丁烷实现给体-受体环丙烷的开环 1-氨基-3-氨甲基化反应。
Ring-Opening 1-Amino-3-aminomethylation of Donor-Acceptor Cyclopropanes via 1,3-Diazepanes.
机构信息
Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106, Braunschweig, Germany.
Technische Universität Braunschweig, Institute of Inorganic and Analytical Chemistry, Hagenring 30, 38106, Braunschweig, Germany.
出版信息
Angew Chem Int Ed Engl. 2017 Jul 24;56(31):9226-9230. doi: 10.1002/anie.201704619. Epub 2017 Jun 28.
The first ring-opening reaction of donor-acceptor cyclopropanes to give diamines is reported. For this reaction, a 1,3-bisfunctionalization was developed using cyclopropanes, triazinanes, and Sc(OTf) as the catalyst, followed by treatment with acid. The reaction proceeds under very mild conditions and tolerates many functional groups. Moreover, a library of various 1,3-diazepanes, which arise as intermediates of the first formal aza-[4+3]-cycloaddition reaction with donor-acceptor cyclopropanes, was synthesized.
本文报道了首例给体-受体环丙烷的开环反应，生成二胺。在该反应中，开发了一种 1,3-双官能化反应，使用环丙烷、三嗪烷和 Sc(OTf)作为催化剂，然后用酸处理。反应在非常温和的条件下进行，并能容忍许多官能团。此外，还合成了各种 1,3-二氮杂环庚烷的库，它们是给体-受体环丙烷与亲双烯体首次进行的[4+3]-环加成反应的中间产物。
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