Enantioselective Intramolecular C-H Insertion Reactions of Donor Donor Metal Carbenoids

被引:124
作者
Soldi, Cristian [1 ]
Lamb, Kellan N. [1 ]
Squitieri, Richard A. [1 ]
Gonzalez-Lopez, Marcos [1 ]
Di Maso, Michael J. [1 ]
Shaw, Jared T. [1 ]
机构
[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA
关键词
CATALYZED DECOMPOSITION; ORGANIC-SYNTHESIS; DIAZO-COMPOUNDS; TOSYLHYDRAZONES; BONDS; DIRHODIUM(II); HOPEAHAINOL; DERIVATIVES; COMPLEXES; SULFONES;
D O I
10.1021/ja508586t
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first asymmetric insertion reactions of donor-donor carbenoids, i.e., those with no pendant electron-withdrawing groups, are reported. This process enables the synthesis of densely substituted benzodihydrofurans with high levels of enantio- and diastereoselectivity. Preliminary results show similar efficiency in the preparation of indanes. This new method is used in the first enantioselective synthesis of an oligoresveratrol natural product (E-delta-viniferin).
引用
收藏
页码:15142 / 15145
页数:4
相关论文
共 45 条
[1]   Synthesis of Sulfones by Iron-Catalyzed Decomposition of Sulfonylhydrazones [J].
Barluenga, Jose ;
Tomas-Gamasa, Maria ;
Aznar, Fernando ;
Valdes, Carlos .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (08) :1520-1526
[2]   Straightforward Synthesis of Ethers: Metal-Free Reductive Coupling of Tosylhydrazones with Alcohols or Phenols [J].
Barluenga, Jose ;
Tomas-Gamasa, Maria ;
Aznar, Fernando ;
Valdes, Carlos .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (29) :4993-4996
[3]   Synthesis of Enol Ethers and Enamines by Pd-Catalyzed Tosylhydrazide-Promoted Cross-Coupling Reactions [J].
Barluenga, Jose ;
Escribano, Maria ;
Moriel, Patricia ;
Aznar, Fernando ;
Valdes, Carlos .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (48) :13291-13294
[4]   Highly enantioselective insertion of carbenoids into o-h bonds of phenols:: An efficient approach to chiral α-aryloxycarboxylic esters [J].
Chen, Chao ;
Zhu, Shou-Fei ;
Liu, Bin ;
Wang, Li-Xin ;
Zhou, Qi-Lin .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (42) :12616-+
[5]   Ruthenium porphyrin catalyzed intramolecular carbenoid C-H insertion. Stereloselective synthesis of cis-disubstituted oxygen and nitrogen heterocycles [J].
Cheung, WH ;
Zheng, SL ;
Yu, WY ;
Zhou, GC ;
Che, CM .
ORGANIC LETTERS, 2003, 5 (14) :2535-2538
[6]  
Davies H.M.L., 2011, ORG REACTIONS, V75, P75
[7]   Asymmetric cyclopropanations by rhodium(II) N-(arylsulfonyl)prolinate catalyzed decomposition of vinyldiazomethanes in the presence of alkenes. Practical enantioselective synthesis of the four stereoisomers of 2-phenylcyclopropan-1-amino acid [J].
Davies, HML ;
Bruzinski, PR ;
Lake, DH ;
Kong, N ;
Fall, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (29) :6897-6907
[8]   Asymmetric intermolecular carbenoid C-H insertions catalyzed by rhodium(II) (S)-N-(p-dodecylphenyl)sulfonylprolinate [J].
Davies, HML ;
Hansen, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (38) :9075-9076
[9]   Application of donor/acceptor-carbenoids to the synthesis of natural products [J].
Davies, Huw M. L. ;
Denton, Justin R. .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3061-3071
[10]   Substituted diaryldiazomethanes and diazofluorenes: structure, reactivity and stability [J].
Davis, Philip J. ;
Harris, Lawrence ;
Karim, Aman ;
Thompson, Amber L. ;
Gilpin, Martin ;
Moloney, Mark G. ;
Pound, Matthew J. ;
Thompson, Claire .
TETRAHEDRON LETTERS, 2011, 52 (14) :1553-1556