Potassium organotrifluoroborates: new partners in catalytic enantioselective conjugate additions to enones

被引:84
作者
Pucheault, M [1 ]
Darses, S [1 ]
Genet, JP [1 ]
机构
[1] Ecole Natl Super Chim Paris, Lab Synth Select Organ & Prod Nat, CNRS, UMR 7573, F-75231 Paris 05, France
关键词
organotrifluoroborates; asymmetric catalysis; 1,4-addition; rhodium catalyst;
D O I
10.1016/S0040-4039(02)01288-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Potassium organotrifluoroborates, highly stable organoboron derivatives and easily accessible from organolithiated reagents, can achieve rhodium(I)-catalyzed asymmetric 1,4-additions to enones using binap as chiral ligand. This reaction proceeds in nearly quantitative yields to afford beta-functionalized ketones with e.e. up to 98%. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6155 / 6157
页数:3
相关论文
共 26 条
[1]  
[Anonymous], COMPREHENSIVE ORGANI
[2]   Potassium alkenyl- and aryltrifluoroborates: Stable and efficient agents for rhodium-catalyzed addition to aldehydes and enones [J].
Batey, RA ;
Thadani, AN ;
Smil, DV .
ORGANIC LETTERS, 1999, 1 (10) :1683-1686
[3]   Cross-coupling reactions of arenediazonium tetrafluoroborates with potassium aryl- or alkenyltrifluoroborates catalyzed by palladium [J].
Darses, S ;
Genet, JP ;
Brayer, JL ;
Demoute, JP .
TETRAHEDRON LETTERS, 1997, 38 (25) :4393-4396
[4]   Potassium vinyltrifluoroborate:: A stable and efficient vinylating agent of arenediazonium salts using palladium catalysts [J].
Darses, S ;
Michaud, G ;
Genêt, JP .
TETRAHEDRON LETTERS, 1998, 39 (28) :5045-5048
[5]  
Darses S, 1999, EUR J ORG CHEM, V1999, P1875
[6]   Rhodium-catalyzed asymmetric conjugate addition of organoboronic acids to nitroalkenes [J].
Hayashi, T ;
Senda, T ;
Ogasawara, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (43) :10716-10717
[7]   Rhodium-catalyzed asymmetric 1,4-addition to 1-alkenylphosphonates [J].
Hayashi, T ;
Senda, T ;
Takaya, Y ;
Ogasawara, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (49) :11591-11592
[8]  
Hayashi T, 2001, SYNLETT, P879
[9]  
Krause N, 2001, SYNTHESIS-STUTTGART, P171
[10]   Cross-coupling reactions of potassium alkyltrifluoroborates with aryl and 1-alkenyl trifluoromethanesulfonates [J].
Molander, GA ;
Ito, T .
ORGANIC LETTERS, 2001, 3 (03) :393-396