Diamidophosphites with remote P*-stereocentres and their performance in Pd-catalyzed enantioselective reactions

被引：22

作者：

Gavrilov, Konstantin N. ^{[1
]}

Zheglov, Sergey V. ^{[1
]}

Gavrilov, Vladislav K. ^{[1
]}

Chuchelkin, Ilya V. ^{[1
]}

Novikov, Ivan M. ^{[1
]}

Shiryaev, Alexei A. ^{[1
]}

Volov, Alexandr N. ^{[2
]}

Zamilatskov, Ilya A. ^{[2
]}

机构：

[1] Ryazan State Univ, Dept Chem, Ryazan 390000, Russia

[2] Russian Acad Sci, AN Frumkin Inst Phys Chem & Electrochem, Moscow 119071, Russia

来源：

TETRAHEDRON-ASYMMETRY | 2014年 / 25卷 / 15期

关键词：

ASYMMETRIC 3+2 CYCLOADDITION; MONODENTATE DIAMIDOPHOSPHITES; ALLYLIC SUBSTITUTION; LIGANDS; APPLICATION; PHOSPHORUS LIGANDS; EFFICIENT LIGANDS; PHOSPHINE LIGANDS; MODULAR APPROACH; HYDROGENATION; ALLYLATION;

D O I：

10.1016/j.tetasy.2014.06.010

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Diamidophosphite ligands based on 1,1'-bis(hydroxymethyl)ferrocene or N-1,N-2-bis((S)-1-hydroxy-3,3-dimethylbutan-2-yl)oxalamide and bearing 1,3,2-diazaphospholidine rings with stereogenic phosphorus atoms were obtained. The use of these ligands provides up to 96% ee in Pd-catalyzed asymmetric allylations of (E)-1,3-diphenylallyl acetate, up to 70% ee in Pd-catalyzed desymmetrizations of N,N'-ditosyl-meso-cyclopent-4-ene-1,3-diol bis-carbamate and up to 80% ee in Pd-catalyzed allylic alkylations of cinnamyl acetate with ethyl 2-oxocyclohexane-1-carboxylate. Results obtained with a diamidophosphite containing an oxalamide framework show the considerable potential of such ligands in enantioselective catalysis. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：1116 / 1121

页数：6

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