Heptamethylindenyl (Ind*) enables diastereoselective benzamidation of cyclopropenes via Rh(III)-catalyzed C-H activation

被引：0
|
作者：
Semakul N. [1 ]
Jackson K.E. [2 ]
Paton R.S. [2 ]
Rovis T. [1 ]
机构：
[1] Department of Chemistry, Colorado State University, Fort Collins, 80523, CO
[2] Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford
来源：
Paton, Robert S. (robert.paton@chem.ox.ac.uk) | 1600年 / Royal Society of Chemistry卷 / 08期
基金：
英国工程与自然科学研究理事会;
关键词：
Bioactive molecules - Building blockes - C-h activation - Cyclopropenes - Diastereo-selectivity - Diastereocontrol - Diastereoselective - Quantum chemical calculations;
D O I：
10.1039/C6SC02587K
中图分类号：
学科分类号：
摘要：
The diastereoselective coupling of O-substituted arylhydroxamates and cyclopropenes mediated by Rh(iii) catalysis was successfully developed. Through ligand development, the diastereoselectivity of this reaction was improved using a heptamethylindenyl (Ind*) ligand, which has been rationalized using quantum chemical calculations. In addition, the nature of the O-substituted ester of benzhydroxamic acid proved important for high diastereoselectivity. This transformation tolerates a variety of benzamides and cyclopropenes that furnish cyclopropa[c]dihydroisoquinolones with high diastereocontrol, which could then be easily transformed into synthetically useful building blocks for pharmaceuticals and bio-active molecules. © The Royal Society of Chemistry.
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页码：1015 / 1020
页数：5
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