Grubbs' Ruthenium-Carbenes Beyond the Metathesis Reaction: Less Conventional Non-Metathetic Utility

被引:284
作者
Alcaide, Benito [1 ]
Almendros, Pedro [2 ]
Luna, Amparo [1 ]
机构
[1] Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
[2] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
关键词
RING-CLOSING METATHESIS; ALLYL PROTECTING GROUP; IN-SITU CONVERSION; OLEFIN-METATHESIS; CROSS-METATHESIS; ENYNE METATHESIS; TANDEM CATALYSIS; RUO4-CATALYZED KETOHYDROXYLATION; ASYMMETRIC-SYNTHESIS; TERMINAL ALKYNES;
D O I
10.1021/cr9001512
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Robert H. Grubbs has developed powerful new catalysts, which is stable in air, for metathesis that enabled custom synthesis of many new molecules. The widely used Grubbs' ruthenium carbene Ru-1, well-known for its ability to promote olefin metathesis, is also an effective catalyst in radical atom transfer reactions such as Kharasch addition. Bicyclic ring systems can be prepared from acyclic dienes through a tandem RCM-intramolecular Kharasch addition reaction sequence. Studies in the group of Quayle have revealed that there is an important rate difference between olefin metathesis and Kharasch reactions in substrates exposed to both reactions conditions. This group suggested that the process requires either direct denaturation of complex Ru-1, which is itself formed as a byproduct of the initial metathesis cycle, or generation of a new ruthenium complex. New uses of the ruthenium-based catalyst are likely, and contribute to its relevance as a versatile and effective tool in organic and organometallic chemistry.
引用
收藏
页码:3817 / 3858
页数:42
相关论文
共 176 条
[11]   Novel ruthenium-catalyzed cleavage of allyl protecting group in lactams [J].
Alcaide, B ;
Almendros, P ;
Alonso, JM .
TETRAHEDRON LETTERS, 2003, 44 (48) :8693-8695
[12]   A novel use of Grubbs' carbene. Application to the catalytic deprotection of tertiary allylamines [J].
Alcaide, B ;
Almendros, P ;
Alonso, JM ;
Aly, MF .
ORGANIC LETTERS, 2001, 3 (23) :3781-3784
[13]   Diversity-oriented preparation of enantiopure spirocyclic 2-azetidinones from α-oxo-β-lactams through barbier-type reactions followed by metal-catalyzed cyclizations [J].
Alcaide, Benito ;
Almendros, Pedro ;
Martinez del Campo, Teresa ;
Rodriguez-Acebes, Raquel .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (4-5) :749-758
[14]   Enantioselective synthesis of piperidine, indolizidine, and quinolizidine alkaloids from a phenylglycinol-derived δ-lactam [J].
Amat, M ;
Llor, N ;
Hidalgo, J ;
Escolano, C ;
Bosch, J .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) :1919-1928
[15]  
[Anonymous], 1992, COMPREHENSIVE HDB HY, DOI DOI 10.1016/C2009-0-11185-6
[16]  
[Anonymous], 1989, Org. React
[17]   Regio- and stereoselective hydrosilylation of terminal alkynes using Grubbs' first-generation olefin-metathesis catalyst [J].
Aricó, CS ;
Cox, LR .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (18) :2558-2562
[18]   Selective isomerization of a terminal olefin catalyzed by a ruthenium complex: The synthesis of indoles through ring-closing metathesis [J].
Arisawa, M ;
Terada, Y ;
Nakagawa, M ;
Nishida, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (24) :4732-4734
[19]   Non-metathesis reactions of ruthenium carbene catalysts and their application to the synthesis of nitrogen-containing heterocycles [J].
Arisawa, Mitsuhiro ;
Terada, Yukiyoshi ;
Takahashi, Kazuyuki ;
Nakagawa, Masako ;
Nishida, Atsushi .
CHEMICAL RECORD, 2007, 7 (04) :238-253
[20]   Development of isomerization and cycloisomerization with use of a ruthenium hydride with N-heterocyclic carbene and its application to the synthesis of heterocycles [J].
Arisawa, Mitsuhiro ;
Terada, Yukiyoshi ;
Takahashi, Kazuyuki ;
Nakagawa, Masako ;
Nishida, Atsushi .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (11) :4255-4261