Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion

被引:1955
作者
Davies, Huw M. L. [1 ]
Manning, James R. [1 ]
机构
[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
关键词
D O I
10.1038/nature06485
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
Novel reactions that can selectively functionalize carbon - hydrogen bonds are of intense interest to the chemical community because they offer new strategic approaches for synthesis. A very promising 'carbon - hydrogen functionalization' method involves the insertion of metal carbenes and nitrenes into C - H bonds. This area has experienced considerable growth in the past decade, particularly in the area of enantioselective intermolecular reactions. Here we discuss several facets of these kinds of C - H functionalization reactions and provide a perspective on how this methodology has affected the synthesis of complex natural products and potential pharmaceutical agents.
引用
收藏
页码:417 / 424
页数:8
相关论文
共 91 条
[1]  
Anada M, 1999, SYNLETT, P1775
[2]   SELECTIVE INTERMOLECULAR CARBON-HYDROGEN BOND ACTIVATION BY SYNTHETIC METAL-COMPLEXES IN HOMOGENEOUS SOLUTION [J].
ARNDTSEN, BA ;
BERGMAN, RG ;
MOBLEY, TA ;
PETERSON, TH .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (03) :154-162
[3]   Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis [J].
Austin, JF ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) :1172-1173
[4]   A stereoselective synthesis of dl-threo-methylphenidate:: Preparation and biological evaluation of novel analogues [J].
Axten, JM ;
Krim, L ;
Kung, HF ;
Winkler, JD .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9628-9629
[5]  
Bergman RG, 2007, NATURE, V446, P391, DOI 10.1038/446391a
[6]   Efficient total syntheses of (-)-colombiasin A and (-)-elisapterosin B: Application of the Cr-catalyzed asymmetric quinone Diels-Alder reaction [J].
Boezio, AA ;
Jarvo, ER ;
Lawrence, BM ;
Jacobsen, EN .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (37) :6046-6050
[7]  
Cesati RR, 2004, J AM CHEM SOC, V126, P96
[8]   Chemistry - A catalytic knight's move [J].
Crabtree, RH .
NATURE, 2006, 441 (7090) :165-166
[9]   Iminoiodanes and C-N bond formation in organic synthesis [J].
Dauban, P ;
Dodd, RH .
SYNLETT, 2003, (11) :1571-1586
[10]   Catalytic asymmetric C-H activation of alkanes and tetrahydrofuran [J].
Davies, HML ;
Hansen, T ;
Churchill, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (13) :3063-3070