Synthesis of Heterocycles through a Ruthenium-Catalyzed Tandem Ring-Closing Metathesis/Isomerization/N-Acyliminium Cyclization Sequence

被引:72
作者
Ascic, Erhad [1 ]
Jensen, Jakob F. [1 ]
Nielsen, Thomas E. [1 ]
机构
[1] Tech Univ Denmark, Dept Chem, DK-2800 Lyngby, Denmark
关键词
cyclization; isomerization; metathesis; ruthenium; tandem reactions; METATHESIS-OLEFIN ISOMERIZATION; IMIDO ALKYLIDENE COMPLEXES; IONS; DERIVATIVES; MOLYBDENUM; REDUCTION; CASCADES;
D O I
10.1002/anie.201100417
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Tandem bicycle: In the title reaction double bonds created during ring-closing metathesis isomerize to generate reactive iminium intermediates that undergo intramolecular cyclization reactions with tethered heteroatom and carbon nucleophiles. In this way, a series of biologically interesting heterocyclic compounds can be made, including a known precursor for the total synthesis of the antiparasitic natural product harmicine. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:5188 / 5191
页数:4
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共 50 条
[1]   Non-metathetic behavior patterns of Grubbs' carbene [J].
Alcaide, B ;
Almendros, P .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (06) :1259-1262
[2]   Grubbs' Ruthenium-Carbenes Beyond the Metathesis Reaction: Less Conventional Non-Metathetic Utility [J].
Alcaide, Benito ;
Almendros, Pedro ;
Luna, Amparo .
CHEMICAL REVIEWS, 2009, 109 (08) :3817-3858
[3]   IBTM-containing gramicidin S analogues: Evidence for IBTM as a suitable type II' beta-turn mimetic [J].
Andreu, D ;
Ruiz, S ;
Carreno, C ;
Alsina, J ;
Albericio, F ;
Jimenez, MA ;
delaFiguera, N ;
Herranz, R ;
GarciaLopez, MT ;
GonzalezMuniz, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (44) :10579-10586
[4]   SYNTHESIS AND PROPERTIES OF PYRROLIN-2-ONES [J].
BAKER, JT ;
SIFNIADES, S .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (15) :2798-2800
[5]   Sequential catalysis: A metathesis/dihydroxylation sequence [J].
Beligny, S ;
Eibauer, S ;
Maechling, S ;
Blechert, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (12) :1900-1903
[6]  
Beligny S., 2006, ANGEW CHEM, V118, P1933
[7]   Novel Supramolecular Palladium Catalyst for the Asymmetric Reduction of Imines in Aqueous Media [J].
da Silva, Wender A. ;
Rodrigues, Manoel T., Jr. ;
Shankaraiah, N. ;
Ferreira, Renan B. ;
Andrade, Carlos Kleber Z. ;
Pilli, Ronaldo A. ;
Santos, Leonardo S. .
ORGANIC LETTERS, 2009, 11 (15) :3238-3241
[8]   Alkene metathesis: the search for better catalysts [J].
Deshmukh, Prashant H. ;
Blechert, Siegfried .
DALTON TRANSACTIONS, 2007, (24) :2479-2491
[9]   Catalyst economy. Part 2: Sequential metathesis-Kharasch sequences using the Grubbs metathesis catalysts [J].
Edlin, CD ;
Faulkner, J ;
Quayle, P .
TETRAHEDRON LETTERS, 2006, 47 (07) :1145-1151
[10]   A catalytic approach to (R)-(+)-muscopyridine with integrated "self-clearance" [J].
Fürstner, A ;
Leitner, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (03) :308-+