Shanghai Key Laboratory of Green Chemistry and Chemical, Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (China).
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032 (China) http://faculty.ecnu.edu.cn/s/1811/t/20975/main.jspy.
Angew Chem Int Ed Engl. 2015 Dec 1;54(49):14849-52. doi: 10.1002/anie.201507165. Epub 2015 Sep 22.
A highly enantioselective gold(I)-catalyzed intermolecular annulation of 2-(1-alkynyl)-2-alken-1-ones with N-allenamides is presented. The present work represents the first example of a gold-catalyzed annulation with the proximal C=C bond of an N-allenamide, and is distinctly different from the previously observed annulations at the distal C=C bond. Interestingly, both enantiomers of the products could be obtained in good yields with high regio-, diastereo-, and enantioselectivity by using either diastereomer of a binol-derived phosphoramidite as a chiral ligand.
本文报道了一种高对映选择性的金（I）催化的 2-（1-炔基）-2-烯-1-酮与 N-烯丙酰胺的分子间环化反应。本工作代表了首例金催化的 N-烯丙酰胺近端 C=C 键环化反应的实例，与先前观察到的远端 C=C 键环化反应明显不同。有趣的是，使用联萘衍生的手性磷酰胺作为手性配体时，两种对映异构体的产物都可以以良好的收率和高区域选择性、非对映选择性和对映选择性获得。
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