Chinese Journal of Organic Chemistry >
Asymmetric N—H Insertion Reaction of α-Diazoesters and Carbamates Co-catalyzed by Dirhodium Acetate, Sufonic Acid and Chiral Sulfonamide Urea
Received date: 2013-10-31
Revised date: 2013-11-25
Online published: 2013-11-28
Supported by
Project supported by the National Natural Science Foundation of China (No. 21125209), the Science and Technology Commission of Shanghai Municipality (No. 12JC1403800) and the Minhang District Government in Shanghai.
The enantioselective N—H insertion of α-diazoesters and carbamates provides a potentially attractive approach to α-amino acid derivatives. Herein, a novel cooperative catalytic system of achiral dirhodium(Ⅱ) acetates, chiral sulfonamide urea and achiral sulfonic acid was developed for asymmetric N—H insertion reactions. Prochiral ammonium ylide intermediates, generated in situ from α-diazoesters and carbamates initiated by dirhodium(Ⅱ) acetate, underwent asymmetric protonation with a considerable enantioselectivity in the presence of chiral sulfonamide urea and achiral sulfonic acid as co-catalysts. The co-catalysts of chiral sulfonamide urea and achiral sulfonic acid were considered as a chiral proton shuttle assisting the asymmetric proton transfer process to control the enantioselectivity. This methodology provides an efficient and mild approach to α-amino acid derivatives in high yields (up to 84% yield) with moderate enantioselectivity (up to 77% ee).
Ni Yi , Guo Xin , Hu Wenhao , Liu Shunying . Asymmetric N—H Insertion Reaction of α-Diazoesters and Carbamates Co-catalyzed by Dirhodium Acetate, Sufonic Acid and Chiral Sulfonamide Urea[J]. Chinese Journal of Organic Chemistry, 2014 , 34(1) : 107 -111 . DOI: 10.6023/cjoc201310053
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