Diastereoselective Carbometalation of Oxa- and Azabicyclic Alkenes under Iron Catalysis

被引：71
作者：
Ito, Shingo [1 ,2 ]
Itoh, Takuma [1 ,2 ]
Nakamura, Masaharu [1 ,2 ]
机构：
[1] Kyoto Univ, Grad Sch Engn, Inst Chem Res, Int Res Ctr Elements Sci, Kyoto 6110011, Japan
[2] Kyoto Univ, Grad Sch Engn, Dept Energy & Hydrocarbon Chem, Kyoto 6110011, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 02期
关键词：
bicyclic alkenes; carbometalation; diastereoselectivity; diphosphine ligands; iron; RING-OPENING REACTIONS; SECONDARY ALKYL-HALIDES; OXABICYCLIC ALKENES; GRIGNARD-REAGENTS; ENANTIOSELECTIVE DESYMMETRIZATION; ASYMMETRIC CYCLODIMERIZATION; UNSATURATED DICARBOXIMIDES; HYDROARYLATION; ALKENYLATION; LIGAND;
D O I：
10.1002/anie.201006180
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Highly diastereoselective carbometalation of oxa- and azabicyclic alkenes with arylzinc reagents has been achieved by using FeCl3 and novel ortho-phenylene diphosphine ligands (see scheme; E=electrophile). The carbozincation products are stable towards β-heteroatom elimination and can be trapped with various electrophiles. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：454 / 457
页数：4
相关论文
共 81 条
[1]   Rhodium-catalyzed asymmetric cyclodimerization of oxabenzonorbornadienes and azabenzonorbornadienes: Scope and limitations [J].
Allen, Anna ;
Le Marquand, Paul ;
Burton, Ryan ;
Villeneuve, Karine ;
Tam, William .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (21) :7849-7857
[2]  
[Anonymous], 2009, ANGEW CHEM
[3]   Aryl Norbornanes and Analogues via Palladium-Catalyzed Hydroarylation with Arenediazonium Tetrafluoroborates [J].
Bartoli, Gabriele ;
Cacchi, Sandro ;
Fabrizi, Giancarlo ;
Goggiamani, Antonella .
SYNLETT, 2008, (16) :2508-2512
[4]   Recent Advances in Iron Catalysis in Organic Synthesis [J].
Bauer, Eike B. .
CURRENT ORGANIC CHEMISTRY, 2008, 12 (16) :1341-1369
[5]   Simple iron-amine catalysts for the cross-coupling of aryl Grignards with alkyl halides bearing β-hydrogens [J].
Bedford, RB ;
Bruce, DW ;
Frost, RM ;
Hird, M .
CHEMICAL COMMUNICATIONS, 2005, (33) :4161-4163
[6]   Iron-catalyzed reactions in organic synthesis [J].
Bolm, C ;
Legros, J ;
Le Paih, J ;
Zani, L .
CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254
[7]   Stereoselective Transformations of meso Bicyclic Hydrazines: Versatile Access to Functionalized Aminocyclopentanes [J].
Bournaud, Chloee ;
Chung, Florence ;
Luna, Alejandro Perez ;
Pasco, Morgane ;
Errasti, Gauthier ;
Lecourt, Thomas ;
Micouin, Laurent .
SYNTHESIS-STUTTGART, 2009, (06) :869-887
[8]   On the Role of Metal Contaminants in Catalyses with FeCl3 [J].
Buchwald, Stephen L. ;
Bolm, Carsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (31) :5586-5587
[9]   Fesulphos-palladium(II) complexes as well-defined catalysts for enantioselective ring opening of meso heterobicyclic alkenes with organozinc reagents [J].
Cabrera, S ;
Arrayás, RG ;
Alonso, I ;
Carretero, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (50) :17938-17947
[10]  
Cahiez G, 1998, SYNTHESIS-STUTTGART, P1199
123456789