手性铑配合物催化的含相邻季碳季碳立体中心的 3,3-二取代氧化吲哚的不对称构筑。
Asymmetric Construction of 3,3-Disubstituted Oxindoles Bearing Vicinal Quaternary-Tertiary Carbon Stereocenters Catalyzed by a Chiral-at-Rhodium Complex.
机构信息
Key Laboratory for Chemical Biology of Fujian Province and Department of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University , Xiamen 361005, People's Republic of China.
Fachbereich Chemie, Philipps-Universität Marburg , Hans-Meerwein-Strasse 4, 35043 Marburg, Germany.
出版信息
J Org Chem. 2017 Jun 16;82(12):6457-6467. doi: 10.1021/acs.joc.7b00793. Epub 2017 Jun 6.
A highly diastereo- and enantioselective synthesis of 3,3-disubstituted oxindoles bearing vicinal quaternary-tertiary carbon centers is enabled by a chiral-at-rhodium Lewis acid catalyst starting from isatin N-protected ketimines and 2-acyl imidazoles. The excellent results with 93-99% yields, diastereoselectivities of 43:1 to >200:1, and high enantioselectivities of 98.4 to >99% confirm the potential of bis-cyclometalated rhodium catalysts for the development of effective asymmetric transformations.
一种手性铑路易斯酸催化剂可以实现高非对映选择性和对映选择性地合成带有相邻季碳-叔碳中心的 3,3-二取代氧化吲哚，该反应由苯并吲哚 N-保护酮亚胺和 2-酰基咪唑起始。结果非常出色，产率为 93-99%，非对映选择性为 43:1 至＞200:1，对映选择性为 98.4 至＞99%，这证实了双环金属化铑催化剂在发展有效不对称转化方面的潜力。
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