Catalytic asymmetric desymmetrization of meso-diamide derivatives through enantioselective N-allylation with a chiral pi-allyl Pd catalyst: improvement and reversal of the enantioselectivity

The Journal of Organic Chemistry
Osamu KitagawaTakeo Taguchi

Abstract

In the presence of the Trost ligands-Pd catalysts, N-monoallylation of bis(2,4,6-triisopropylbenzne)sulfonylamides derived from meso-1,2-diamines proceeds with good to excellent enantioselectivity (85-96% ee) to give asymmetric desymmetrization products. Under the same conditions, in the reaction with meso-bistolunesulfonylamide derivatives, reversal of the enantioselectivity is observed.

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Citations

Sep 16, 2011·Angewandte Chemie·Robert H SnellMichael C Willis
Dec 4, 2012·Chemistry : a European Journal·Robert H SnellMichael C Willis
Nov 28, 2012·Angewandte Chemie·Naoya Kumagai, Masakatsu Shibasaki
Feb 24, 2009·Journal of the American Chemical Society·Akihiro NojiriMasakatsu Shibasaki
Aug 26, 2011·Journal of the American Chemical Society·Chandra Kanta De, Daniel Seidel
Apr 21, 2018·Chemical Reviews·Irina P BeletskayaMiguel Yus
Jan 25, 2007·Journal of the American Chemical Society·Wei ZengYu-Xue Li

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