Nickel-catalyzed asymmetric Negishi cross-couplings of secondary allylic chlorides with alkylzincs

被引:195
作者
Son, Sunghee [1 ]
Fu, Gregory C. [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
D O I
10.1021/ja800103z
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Complementing previous advances in allylation chemistry, an effective nickel/Pybox catalyst for regioselective asymmetric Negishi cross-couplings of racemic secondary allylic chlorides with readily available organozinc halides has been developed. The method has been applied in two key steps of a formal total synthesis of fluvirucinine A(1).
引用
收藏
页码:2756 / +
页数:3
相关论文
共 21 条
[1]   Catalytic enantioselective Negishi reactions of racemic secondary benzylic halides [J].
Arp, FO ;
Fu, GC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (30) :10482-10483
[2]   Nickel-catalyzed allylation of lithium 1-alkynyl(trialkoxy)borates with 1,3-disubstituted allyl carbonates [J].
Chen, H ;
Deng, MZ .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 603 (02) :189-193
[3]   Nickel(0)-catalyzed asymmetric cross-coupling reactions of allylic compounds with arylboronic acids [J].
Chung, KG ;
Miyake, Y ;
Uemura, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (01) :15-18
[4]   NICKEL CATALYZED ASYMMETRIC COUPLING REACTION BETWEEN ALLYL PHENYL ETHERS AND GRIGNARD-REAGENTS [J].
CONSIGLIO, G ;
MORANDINI, F ;
PICCOLO, O .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (03) :112-114
[5]  
Dübner F, 1999, ANGEW CHEM INT EDIT, V38, P379, DOI 10.1002/(SICI)1521-3773(19990201)38:3<379::AID-ANIE379>3.0.CO
[6]  
2-Y
[7]  
Fagnou K, 2002, ANGEW CHEM INT EDIT, V41, P26, DOI 10.1002/1521-3773(20020104)41:1<26::AID-ANIE26>3.0.CO
[8]  
2-9
[9]   Asymmetric nickel-catalyzed negishi cross-couplings of secondary α-bromo amides with organozinc reagents [J].
Fischer, C ;
Fu, GC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4594-4595
[10]   Enantioselective preparation of β,β-disubstituted α-methylenepropionates by MAO promotion of the zinc Schlenk equilibrium [J].
Goldsmith, PJ ;
Teat, SJ ;
Woodward, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (15) :2235-2237