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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
来源:
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.
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页码:37 / 43
页数:7
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