Nickel-Catalyzed Allylation of a-Amido Sulfones To Form Protected Homoallylic Amines

被引:11
作者
Caputo, Jill A. [1 ]
Naodovic, Marina [1 ]
Weix, Daniel J. [1 ]
机构
[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA
关键词
nickel; allylation; amines; imines; reduction; TERT-BUTANESULFINYL IMINES; ASYMMETRIC ALLYLATION; MEDIATED ALLYLATION; ENANTIOSELECTIVE ALLYLATION; STEREOSELECTIVE-SYNTHESIS; REDUCTIVE ALLYLATION; ALLYLIC CARBONATES; AQUEOUS-MEDIA; IN-SITU; HYDRAZONES;
D O I
10.1055/s-0034-1379539
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The allylation of stable, protected imine precursors, a-amiclo sulfones, with allylic acetates to form homoallylic amines is catalyzed by nickel under mild reducing conditions. Aliphatic and aryl imMes are tolerated, as are substituted allylic acetates. In the case of substituted allylic acetates, high diastereoselectivity and regioselectivity is observed in some cases and the branched product is obtained almost exclusively.
引用
收藏
页码:323 / 326
页数:4
相关论文
共 46 条
[1]   Stereoselective allylboration of imines and indoles under mild conditions. An in situ E/Z isomerization of imines by allylboroxines [J].
Alam, Rauful ;
Das, Arindam ;
Huang, Genping ;
Eriksson, Lars ;
Himo, Fahmi ;
Szabo, Kalman J. .
CHEMICAL SCIENCE, 2014, 5 (07) :2732-2738
[2]   Diene-Ligated Iridium Catalyst for Allylation Reactions of Ketones and Imines [J].
Barker, Timothy J. ;
Jarvo, Elizabeth R. .
ORGANIC LETTERS, 2009, 11 (05) :1047-1049
[3]   Diastereoselective allylation and crotylation of N-tert-butanesulfinyl imines with allylic alcohols [J].
Barros, Olga Soares do Rego ;
Sirvent, Juan Alberto ;
Foubelo, Francisco ;
Yus, Miguel .
CHEMICAL COMMUNICATIONS, 2014, 50 (52) :6898-6901
[4]   A concise stereoselective synthesis of Preussin, 3-epi-Preussin, and analogues [J].
Bertrand, Myra Beaudoin ;
Wolfe, John P. .
ORGANIC LETTERS, 2006, 8 (11) :2353-2356
[5]   Enantioselective Addition of Boronates to Acyl Imines Catalyzed by Chiral Biphenols [J].
Bishop, Joshua A. ;
Lou, Sha ;
Schaus, Scott E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (24) :4337-4340
[6]   Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].
Bloch, R .
CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438
[7]  
BROWN DS, 1990, SYNLETT, P48
[8]   Chemistry of Organomanganese(II) Compounds [J].
Cahiez, Gerard ;
Duplais, Christophe ;
Buendia, Julien .
CHEMICAL REVIEWS, 2009, 109 (03) :1434-1476
[9]   Indium(I)-Catalyzed Asymmetric Allylation, Crotylation, and α-Chloroallylation of Hydrazones with Rare Constitutional and High Configurational Selectivities [J].
Chakrabarti, Ananya ;
Konishi, Hideyuki ;
Yamaguchi, Miyuki ;
Schneider, Uwe ;
Kobayashi, Shu .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (10) :1838-1841
[10]   Stereocontrol in Synthesis of Homoallylic Amines. Syn Selective Direct Allylation of Hydrazones with Allylboronic Acids [J].
Das, Arindam ;
Alam, Rauful ;
Eriksson, Lars ;
Szabo, Kalman J. .
ORGANIC LETTERS, 2014, 16 (14) :3808-3811