Nickel-Catalyzed Cycloaddition of 1,3-Dienes with 3-Azetidinones and 3-Oxetanones

被引:60
作者
Thakur, Ashish [1 ]
Facer, Megan E. [1 ]
Louie, Janis [1 ]
机构
[1] Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA
关键词
azetidinones; CC activation; cycloaddition; nickel; oxetanones; C-C BOND; ALDEHYDE OXIDATION LEVEL; FORMING TRANSFER HYDROGENATION; STEREOSELECTIVE CONSTRUCTION; COUPLING REACTIONS; OLEFIN INSERTION; RUTHENIUM; ALKYNES; ALCOHOL; DIENES;
D O I
10.1002/anie.201306869
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A growth and expansion strategy: A Ni/P(p-tol)3-catalyzed cycloaddition of 1,3-dienes with 3-azetidinones and 3-oxetanones produced eight-membered heterocycles with a variety of substituents (see scheme; Boc=tert-butoxycarbonyl). The synthesis of the reduced azocine and oxocine derivatives involved the challenging steps of C(sp2)-C(sp 3) bond activation and C(sp3)-C(sp3) reductive elimination. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:12161 / 12165
页数:5
相关论文
共 119 条
[1]  
[Anonymous], 2012, ANGEW CHEM
[2]  
[Anonymous], 2004, ANGEW CHEM
[3]   Nickel-catalyzed [4+2+2]-type annulation reaction of cyclobutanones with diynes and enynes [J].
Ashida, Shinji ;
Murakami, Masahiro .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2008, 81 (07) :885-893
[4]   A Nickel-Catalyzed Benzannulation Approach to Aromatic Boronic Esters [J].
Auvinet, Anne-Laure ;
Harrity, Joseph P. A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (12) :2769-2772
[5]   CYCLOBUTANONES AND CYCLOBUTENONES IN NATURE AND IN SYNTHESIS [J].
BELLUS, D ;
ERNST, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (06) :797-827
[6]  
Bellus D., 1988, ANGEW CHEM, V100, P820, DOI DOI 10.1002/ANGE.19881000607
[7]   Synthesis of macrocycles via cobalt-mediated [2+2+2] cycloadditions [J].
Boñaga, LVR ;
Zhang, HC ;
Moretto, AF ;
Ye, H ;
Gauthier, DA ;
Li, J ;
Leo, GC ;
Maryanoff, BE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (10) :3473-3485
[8]   Iridium(I)-catalyzed cycloisomerization of enynes [J].
Chatani, N ;
Inoue, H ;
Morimoto, T ;
Muto, T ;
Murai, S .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (12) :4433-4436
[9]   Stereoselective Borylative Ketone-Diene Coupling [J].
Cho, Hee Yeon ;
Yu, Zhiyong ;
Morken, James P. .
ORGANIC LETTERS, 2011, 13 (19) :5267-5269
[10]   Ni-Catalyzed Borylative Diene-Aldehyde Coupling: The Remarkable Effect of P(SiMe3)3 [J].
Cho, Hee Yeon ;
Morken, James P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (22) :7576-+