使用 Br/Cl 促进炔丙羧酸酯的区域选择性金催化重排：（1Z, 3E）-1-溴/氯-2-羧基-1,3-二烯的高效合成。
The use of Br/Cl to promote regioselective gold-catalyzed rearrangement of propargylic carboxylates: an efficient synthesis of (1Z, 3E)-1-bromo/chloro-2-carboxy-1,3-dienes.
机构信息
Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA 93106, USA.
出版信息
Chem Commun (Camb). 2010 Dec 28;46(48):9179-81. doi: 10.1039/c0cc03669b. Epub 2010 Oct 29.
Abstract
A gold-catalyzed synthesis of 1-bromo/chloro-2-carboxy-1,3-dienes is developed using propargylic carboxylates containing halogenated alkynes as substrates. The reaction is highly diastereoselective, and the halogen atom at the alkyne terminus selectively promotes a 1,2-acyloxy migration. The diene products participate in the Diels-Alder and cross-coupling reactions.
摘要
发展了一种使用含卤素炔烃的丙炔酸酯作为底物的金催化合成 1-溴/氯-2-羧基-1,3-二烯的方法。该反应具有高度的非对映选择性，炔烃末端的卤素原子选择性地促进 1,2-烷氧基迁移。二烯产物参与 Diels-Alder 和交叉偶联反应。
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