Reactions of metallocarbenes derived from N-sulfonyl-1,2,3-triazoles

被引:544
作者
Davies, Huw M. L. [1 ]
Alford, Joshua S. [1 ]
机构
[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA
基金
美国国家科学基金会;
关键词
RHODIUM(II) AZAVINYL CARBENES; RH-CATALYZED TRANSANNULATION; TERMINAL ALKYNES; SULFONYL AZIDES; RING EXPANSION; REARRANGEMENT; TRIAZOLES; ANNULATION; REACTIVITY; PYRROLES;
D O I
10.1039/c4cs00072b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Metal-stabilized carbenes derived from diazo compounds have become broadly useful reactive intermediates for organic synthesis. This tutorial review will describe the recent advances in using N-sulfonyl-1,2,3-triazoles as precursors for the formation of metal-bound imino carbene intermediates. These intermediates undergo a variety of synthetically useful transformations, which include transannulation reactions to generate new heterocycles, cyclopropanation and subsequent ring expansions, ylide formation with subsequent rearrangements, and C-H functionalization. Furthermore, many of these transformations can be conducted with high levels of enantioselectivity by use of chiral rhodium(II) catalysts.
引用
收藏
页码:5151 / 5162
页数:12
相关论文
共 55 条
[1]   Conversion of Cyclic Ketones to 2,3-Fused Pyrroles and Substituted Indoles [J].
Alford, Joshua S. ;
Spangler, Jillian E. ;
Davies, Huw M. L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (32) :11712-11715
[2]   Expanding the Scope of Donor/Acceptor Carbenes to N-Phthalimido Donor Groups: Diastereoselective Synthesis of 1-Cyclopropane α-Amino Acids [J].
Alford, Joshua S. ;
Davies, Huw M. L. .
ORGANIC LETTERS, 2012, 14 (23) :6020-6023
[3]  
[Anonymous], 2012, ANGEW CHEM-GER EDIT
[4]   Rhodium(II)-Catalyzed Stereocontrolled Synthesis of Dihydrofuran-3-imines from 1-Tosyl-1,2,3-triazoles [J].
Boyer, Alistair .
ORGANIC LETTERS, 2014, 16 (06) :1660-1663
[5]  
Carreira E.M., 2009, Classics in Stereoselective Synthesis, P1
[6]   Transition-Metal-Catalyzed Denitrogenative Transannulation: Converting Triazoles into Other Heterocyclic Systems [J].
Chattopadhyay, Buddhadeb ;
Gevorgyan, Vladimir .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (04) :862-872
[7]   Rh-Catalyzed Transannulation of N-Tosyl-1,2,3-Triazoles with Terminal Alkynes [J].
Chattopadhyay, Buddhadeb ;
Gevorgyan, Vladimir .
ORGANIC LETTERS, 2011, 13 (14) :3746-3749
[8]   Rh-catalyzed transannulation of pyridotriazoles with alkynes and nitriles [J].
Chuprakov, Stepan ;
Hwang, Frank W. ;
Gevorgyan, Vladimir .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (25) :4757-4759
[9]   Stereoselective 1,3-Insertions of Rhodium(II) Azavinyl Carbenes [J].
Chuprakov, Stepan ;
Worrell, Brady T. ;
Selander, Nicklas ;
Sit, Rakesh K. ;
Fokin, Valery V. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (01) :195-202
[10]   Transannulation of 1-Sulfonyl-1,2,3-triazoles with Heterocumulenes [J].
Chuprakov, Stepan ;
Kwok, Sen Wai ;
Fokin, Valery V. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (12) :4652-4655