Dearomatization of Electron-Deficient Nitrogen Heterocycles via Cobalt-Catalyzed Asymmetric Cyclopropanation

被引:16
作者
Joshi-Pangu, Amruta [1 ]
Cohen, Ryan D. [1 ]
Tudge, Matthew T. [1 ]
Chen, Yonggang [1 ]
机构
[1] Merck & Co Inc, Dept Proc & Analyt Chem, POB 2000, Rahway, NJ 07065 USA
关键词
IN-SITU GENERATION; INTRAMOLECULAR CYCLOPROPANATION; CHIRAL LIGANDS; ENANTIOSELECTIVE CYCLOPROPANATION; OLEFIN CYCLOPROPANATION; CONSTRUCTION; DIAZOMETHANE; COMPLEXES; PEPTIDOMIMETICS; DIAZOACETATES;
D O I
10.1021/acs.joc.6b00322
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The dearomatization of a series of electron-deficient nitrogen heterocycles has been achieved through a cobalt-catalyzed asymmetric cyclopropanation reaction. This reaction proceeds with high levels of enantio- and diastereoselectivity to afford unique cyclopropanes that can be further functionalized to provide complex heterocyclic building blocks.
引用
收藏
页码:3070 / 3075
页数:6
相关论文
共 37 条
[1]   Asymmetric Cyclopropanation Reactions [J].
Bartoli, Giuseppe ;
Bencivenni, Giorgio ;
Dalpozzo, Renato .
SYNTHESIS-STUTTGART, 2014, 46 (08) :979-1029
[2]   (1aR,5aR)1a,3,5,5a-Tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic Acid (MK-1903): A Potent GPR109a Agonist that Lowers Free Fatty Acids in Humans [J].
Boatman, P. Douglas ;
Lauring, Brett ;
Schrader, Thomas O. ;
Kasem, Michelle ;
Johnson, Benjamin R. ;
Skinner, Philip ;
Jung, Jae-Kyu ;
Xu, Jerry ;
Cherrier, Martin C. ;
Webb, Peter J. ;
Semple, Graeme ;
Sage, Carleton R. ;
Knudsen, Jens ;
Chen, Ruoping ;
Luo, Wen-Lin ;
Caro, Luzelena ;
Cote, Josee ;
Lai, Eseng ;
Wagner, John ;
Taggart, Andrew K. ;
Carballo-Jane, Ester ;
Hammond, Milton ;
Colletti, Steven L. ;
Tata, James R. ;
Connolly, Daniel T. ;
Waters, M. Gerard ;
Richman, Jeremy G. .
JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (08) :3644-3666
[3]   Bis(oxazoline)-copper(I)-catalyzed enantioselective cyclopropanation of cinnamate esters with diazomethane [J].
Charette, AB ;
Janes, MK ;
Lebel, H .
TETRAHEDRON-ASYMMETRY, 2003, 14 (07) :867-872
[4]   Asymmetric inter- and intramolecular cyclopropanation of alkenes catalyzed by chiral ruthenium porphyrins. Synthesis and crystal structure of a chiral metalloporphyrin carbene complex [J].
Che, CM ;
Huang, JS ;
Lee, FW ;
Li, Y ;
Lai, TS ;
Kwong, HL ;
Teng, PF ;
Lee, WS ;
Lo, WC ;
Peng, SM ;
Zhou, ZY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (18) :4119-4129
[5]   Recent advances in the total synthesis of cyclopropane-containing natural products [J].
Chen, David Y. -K. ;
Pouwer, Rebecca H. ;
Richard, Jean-Alexandre .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (13) :4631-4642
[6]   Olefin Cyclopropanation via Carbene Transfer Catalyzed by Engineered Cytochrome P450 Enzymes [J].
Coelho, Pedro S. ;
Brustad, Eric M. ;
Kannan, Arvind ;
Arnold, Frances H. .
SCIENCE, 2013, 339 (6117) :307-310
[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]   DIRHODIUM(II) TETRAKIS(CARBOXAMIDATES) WITH CHIRAL LIGANDS - STRUCTURE AND SELECTIVITY IN CATALYTIC METAL CARBENE TRANSFORMATIONS [J].
DOYLE, MP ;
WINCHESTER, WR ;
HOORN, JAA ;
LYNCH, V ;
SIMONSEN, SH ;
GHOSH, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :9968-9978
[9]   BIS(OXAZOLINES) AS CHIRAL LIGANDS IN METAL-CATALYZED ASYMMETRIC REACTIONS - CATALYTIC, ASYMMETRIC CYCLOPROPANATION OF OLEFINS [J].
EVANS, DA ;
WOERPEL, KA ;
HINMAN, MM ;
FAUL, MM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :726-728
[10]   CHIRAL COPPER SEMICORRIN COMPLEXES AS ENANTIOSELECTIVE CATALYSTS FOR THE CYCLOPROPANATION OF OLEFINS BY DIAZO-COMPOUNDS [J].
FRITSCHI, H ;
LEUTENEGGER, U ;
PFALTZ, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (11) :1005-1006