RECENT ADVANCES ON THE SYNTHESIS OF PIPERIDINES THROUGH RUTHENIUM-CATALYZED RING-CLOSING METATHESIS (RCM) REACTIONS

被引：32

作者：

Merino, Pedro ^{[1
]}

Tejero, Tomas ^{[1
]}

Greco, Graziella ^{[1
]}

Marca, Eduardo ^{[1
]}

Delso, Ignacio ^{[1
,2
]}

Gomez-SanJuan, Asier ^{[1
]}

Matute, Rosa ^{[3
]}

机构：

[1] Univ Zaragoza, CSIC, Dept Organ Chem, E-50009 Zaragoza, Aragon, Spain

[2] Univ Zaragoza, CSIC, NMR Serv,CEQMA, Inst Chem Synth & Homogeneous Catalysis ISQCH, E-50009 Zaragoza, Aragon, Spain

[3] Univ Zaragoza, Dept Chem Engn & Environm Technol, E-50018 Zaragoza, Aragon, Spain

来源：

HETEROCYCLES | 2012年 / 84卷 / 01期

关键词：

Ring-Closing Metathesis; Piperidine; Nitrogen Heterocycle; Alkaloid; Indolizidine; BIASED 3,3-SIGMATROPIC REARRANGEMENT; AMINO-ACID-DERIVATIVES; METAL-CARBON BONDS; OLEFIN-METATHESIS; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; EFFICIENT SYNTHESIS; 1-DEOXYNOJIRIMYCIN ANALOGS; 3-HYDROXYPIPECOLIC ACID;

D O I：

10.3987/REV-11-SR(P)1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ring-closing metathesis reactions of dialkenyl amines, amides and carbamates catalyzed by Ru-catalysts provide efficient approaches to six-membered nitrogen heterocyclic compounds, which are precursors of a variety of natural products and related compounds.

引用

页码：75 / 100

页数：26

共 130 条

[1] Modular asymmetric synthesis of functionalized azaspirocycles based on the sulfoximine auxiliary [J].

Adrien, Adeline ;

Gais, Hans-Joachim ;

Koehler, Franz ;

Runsink, Jan ;

Raabe, Gerhard .

ORGANIC LETTERS, 2007, 9 (11) :2155-2158

[2] Asymmetric synthesis of cis-4- and trans-3-hydroxypipecolic acids [J].

Alegret, Carlos ;

Ginesta, Xavier ;

Riera, Antoni .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (10) :1789-1796

[3]

[Anonymous], 2007, ADV SYNTH CATAL OLEF, V349, P1

[4] Asymmetric syntheses of (-)-lentiginosine and an original pyrrolizidinic analogue thereof from a versatile epoxyamine intermediate [J].

Ayad, T ;

Génisson, Y ;

Baltas, M .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (14) :2626-2631

[5] Asymmetrized tris(hydroxymethyl)methane as a precursor of N- and O-containing 6-membered heterocycles through ring-closing metathesis [J].

Banfi, L ;

Guanti, G ;

Paravidino, M ;

Riva, R .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (09) :1729-1737

[6] Synthesis of sedamine by cycloisomerisation of an allenic hydroxylamine [J].

Bates, Roderick W. ;

Nemeth, Joseph A. ;

Snell, Robert H. .

SYNTHESIS-STUTTGART, 2008, (07) :1033-1038

[7] A New Acyl Radical-based Route to the 1,5-Methanoazocino[4,3-b]indole Framework of Uleine and Strychnos Alkaloids [J].

Bennasar, M. -Lluisa ;

Roca, Tomas ;

Garcia-Diaz, Davinia .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22) :9033-9039

[8] 6-Exo cyclizations of 2-indolylacyl radicals:: Access to the uleine alkaloid skeleton [J].

Bennasar, M. -Lluisa ;

Roca, Tomas ;

Garcia-Diaz, Davinia .

SYNLETT, 2008, (10) :1487-1490

[9] Synthesis of carboxylic amides by ring-opening of oxazolidinones with Grignard reagents [J].

Bensa, David ;

Coldham, Iain ;

Feinaeugle, Pia ;

Pathaka, Ravindra B. ;

Butlin, Roger J. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (08) :1410-1415

[10] A highly practical RCM approach towards a molecular building kit of spirocyclic reverse turn mimics [J].

Bittermann, Holger ;

Boeckler, Frank ;

Einsiedel, Hirgen ;

Gmeiner, Peter .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (24) :6315-6322

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