Asymmetric synthesis and absolute configuration of a planar chiral phosphapalladacycle with a ferrocenyl framework

被引:8
作者
Gorunova, Olga N. [2 ]
Livantsov, Michail V. [1 ]
Grishin, Yuri K. [1 ]
Kataeva, Nadezhda A. [3 ]
Kochetkov, Konstantin A. [2 ]
Churakov, Andrei V. [3 ]
Kuz'mina, Lyudmila G. [3 ]
Dunina, Valery V. [1 ]
机构
[1] Moscow MV Lomonosov State Univ, Dept Chem, Lenin Hills 1,GSP-2, Moscow 119991, Russia
[2] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Moscow 119991, Russia
[3] Russian Acad Sci, NS Kurnakov Inst Gen & Inorgan Chem, Moscow 119991, Russia
关键词
Planar chirality; Central chirality; Phosphapalladacycles; Crystal structures; Asymmetric synthesis; Stereoselective substitution; OPTICALLY-ACTIVE PHOSPHAPALLADACYCLES; ENANTIOMERIC PURITY DETERMINATION; AZA-CLAISEN REARRANGEMENT; ALPHA-AMINO-ACIDS; NMR-SPECTROSCOPY; PROMOTED HYDROPHOSPHINATION; FUNCTIONALIZED PHOSPHINES; CYCLOPALLADATED LIGANDS; PALLADIUM COMPLEXES; X-RAY;
D O I
10.1016/j.poly.2011.08.026
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A monodentate optically active tertiary alpha-ferrocenylethylphosphine was prepared from the corresponding tertiary a-ferrocenylethylamine; Me2N group substitution by a tert-Bu2P group occurs with complete retention of the enantiomeric composition and absolute configuration of the alpha-carbon stereocentre. The cyclopalladation of this phosphine ligand results in the formation of a phosphapalladacycle bearing the elements of central and planar chirality with a high diastereoselectivity. The enantiomeric composition of the CP-palladacycle was determined by P-31{H-1} NMR spectroscopy using (S)-prolinate as a chiral derivatizing agent. The structure and absolute configuration of the phosphapalladacycle were established using NMR spectroscopy and an X-ray diffraction study of its (S)-prolinate derivative. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:37 / 43
页数:7
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