Enantioselective synthesis of alpha-phosphinoketones

被引:12
作者
Enders, D
Berg, T
Raabe, G
Runsink, J
机构
关键词
D O I
10.1002/hlca.19960790112
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first asymmetric (C-P)-connective synthesis of alpha-phosphinoketones in high enantiomeric purity (e.e. 91-97 %) is described. Key step is the highly diastereoselective phosphinylation of SAMP-hydrazones (S)-2 to produce alpha-phosphinohydrazones (S,R)-3, isolated as the more stable borane adducts. Subsequent ozonolysis afforded the title compounds (R)-4, potential ligands for enantioselective homogeneous catalysis.
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页码:118 / 122
页数:5
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共 52 条
[41]  
REETZ MT, 1977, LIEBIGS ANN CHEM, V242
[42]  
SAVIGNAC P, 1976, TETRAHEDRON LETT, P2829
[43]   NEW PHOSPHANEBORANE CHEMISTRY [J].
SCHMIDBAUR, H .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 200 (01) :287-306
[44]  
SCHMIDBAUR H, 1979, ANGEW CHEM INT EDIT, V18, P781, DOI 10.1002/anie.197907811
[45]  
SCHMIDBAUR H, 1979, ANGEW CHEM, V91, P847
[46]   SYNTHESIS AND COORDINATION PROPERTIES OF NOVEL POLYFUNCTIONAL PHOSPHINE-LIGANDS [J].
SOULIVONG, D ;
MATT, D ;
ZIESSEL, R ;
DOUCE, L ;
DESCHENAUX, R .
TETRAHEDRON LETTERS, 1993, 34 (07) :1151-1154
[47]  
STEPANOV IA, 1979, ZH OBSHCH KHIM+, V49, P2389
[48]   IMPROVED PROCEDURE FOR PREPARATION OF OPTICALLY-ACTIVE 3-HYDROXYGLUTARATE MONOESTERS AND 3-HYDROXY-5-OXOALKANOIC ACIDS [J].
THEISEN, PD ;
HEATHCOCK, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (10) :2374-2378
[49]  
Torr R. S., 1979, J CHEM SOC PAKISTAN, V1, P15
[50]  
Wadsworth W. S., 1977, ORGANIC REACTIONS, V25