Chinese Journal of Organic Chemistry >
Synthesis of Chirl N,P-ligands Derived from L-Proline and Its Application to 1,3-Dipolar Cycloaddition
Received date: 2013-01-31
Revised date: 2013-02-26
Online published: 2013-03-01
Supported by
Project supported by the National Natural Science Foundation of China (No. 20902015) and the Fundamental Research Funds for the Central Universities (No. 2010055).
Aminophosphine 2 was obtained by deprotection of amidophosphine 1, which was derived from L-proline. Deprotonation of aminophosphine 2 with n-BuLi, and then being captured by 2-MeO-pyridine gave chiral pyridyl N,P-ligands 4. Reaction of aminoalcohol and diethyl carbonate afforded oxazolidione 6, which was converted to compounds 7 by the reaction with triethyloxonium tetrafluoroborate. Chiral N,P-ligands 8 were obtained by the reaction of compounds 7 with aminophosphine 2. Two kinds of chiral N,P-ligands shown excellent catalytic activity in Ag(I) catalytic asymmetric 1,3-dipolar cycloaddition, and up to 93% yield and 15% ee were obtained.
Chen Hong , Chen Qian . Synthesis of Chirl N,P-ligands Derived from L-Proline and Its Application to 1,3-Dipolar Cycloaddition[J]. Chinese Journal of Organic Chemistry, 2013 , 33(04) : 848 -853 . DOI: 10.6023/cjoc201301080
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