双 CuH 和 Pd 催化的高取代 1,3-二烯的立体选择性合成。
A Dual CuH- and Pd-Catalyzed Stereoselective Synthesis of Highly Substituted 1,3-Dienes.
机构信息
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
出版信息
Org Lett. 2021 Nov 19;23(22):8816-8821. doi: 10.1021/acs.orglett.1c03324. Epub 2021 Nov 2.
Abstract
Conjugated dienes are versatile building blocks and prevalent substructures in synthetic chemistry. Herein, we report a method for the stereoselective hydroalkenylation of alkynes, utilizing readily available enol triflates. We leveraged an -generated and geometrically pure vinyl-Cu(I) species to form the ,- or ,-1,3-dienes in excellent stereoselectivity and yield. This approach allowed for the synthesis of highly substituted -dienes, including pentasubstituted 1,3-dienes, which are difficult to prepare by existing approaches.
摘要
共轭二烯是多功能的结构单元，也是合成化学中常见的结构基元。在此，我们报告了一种利用易得的烯醇三氟甲磺酸酯对炔烃进行立体选择性氢烯丙基化的方法。我们利用 - 生成的、立体纯的乙烯基 -Cu(I)物种形成了,- 或,-1,3-二烯，具有优异的立体选择性和产率。该方法可用于合成高度取代的 - 二烯，包括难以用现有方法制备的五取代 1,3-二烯。
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