Highly diastereoselective preparation of (E)-alkenylsilanes bearing an α-chiral center

被引:34
作者
Perrone, Sylvie [1 ]
Knochel, Paul [1 ]
机构
[1] Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
关键词
D O I
10.1021/ol063097o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The copper(I)-mediated anti-S(N)2' allylic substitution allows a highly stereoselective preparation of alkenylsilanes bearing a chiral center in the alpha-position with high transfer of chirality. These alkenylsilanes were converted into alpha,beta-unsaturated ketones or into the corresponding boronic esters without loss of the chiral information.
引用
收藏
页码:1041 / 1044
页数:4
相关论文
共 73 条
[1]   Diastereoselective alkylation of (arene)tricarbonylchromium and ferrocene complexes using a chiral, C2-symmetrical 1,2-diamine as auxiliary [J].
Alexakis, A ;
Tomassini, A ;
Andrey, O ;
Bernardinelli, G .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (07) :1332-1339
[2]   Tandem copper-catalyzed enantioselective allylation-metathesis [J].
Alexakis, A ;
Croset, K .
ORGANIC LETTERS, 2002, 4 (23) :4147-4149
[3]  
Alexakis A, 2001, SYNLETT, P927
[4]   The direct use of phenyldimethylsilanes in silicon assisted palladium catalysed cross coupling [J].
Anderson, JC ;
Anguille, S ;
Bailey, R .
CHEMICAL COMMUNICATIONS, 2002, (18) :2018-2019
[5]   A straightforward route to polyenylsilanes by palladium- or nickel-catalyzed cross-coupling reactions [J].
Babudri, F ;
Farinola, GM ;
Fiandanese, V ;
Mazzone, L ;
Naso, F .
TETRAHEDRON, 1998, 54 (07) :1085-1094
[6]   Stereoselective reactions of acyclic allylic phosphates with organocopper reagents [J].
Belelie, JL ;
Chong, JM .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (16) :5552-5555
[7]   Stereospecific and stereodivergent construction of quaternary carbon centers through switchable directed/nondirected allylic substitution [J].
Breit, B ;
Demel, P ;
Studte, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (29) :3786-3789
[8]   Iterative deoxypropionate synthesis based on a copper-mediated directed allylic substitution [J].
Breit, B ;
Herber, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (29) :3790-3792
[9]  
Breit B, 2001, ADV SYNTH CATAL, V343, P429, DOI 10.1002/1615-4169(200107)343:5<429::AID-ADSC429>3.3.CO
[10]  
2-B