N-Heterocycles from Chromium Aminocarbenes

被引：6

作者：

Dery, Martin ^{[1
]}

Assouvie, Kevin ^{[1
]}

Heinrich, Nora ^{[1
]}

Rajotte, Isabelle ^{[1
]}

Lefebvre, Louis-Philippe D. ^{[1
]}

Legault, Marc-Andre ^{[1
]}

Spino, Claude ^{[1
]}

机构：

[1] Univ Sherbrooke, Dept Chim, Sherbrooke, PQ J1K 2R1, Canada

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 05期

基金：

加拿大自然科学与工程研究理事会;

关键词：

FISCHER CARBENE COMPLEXES; PHOTOLYTIC REACTION; BETA-LACTAMS; (AMINOCARBENE)CHROMIUM(0) COMPLEXES; ALKYNES; IMINES; AMIDES; CYCLOPROPANATION; NUCLEOPHILES; DERIVATIVES;

D O I：

10.1021/acs.orglett.5b00313

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The initial [2 + 2]-cycloadduct between a chromium aminocarbene and a tethered alkene undergoes a beta-hydrogen elimination very efficiently when triphenylphosphine is added as a ligand. The reaction gives cyclic enamines or homoenamines depending on the substitution on the alkene.

引用

页码：1312 / 1315

页数：4

共 47 条

[1] Multi-component reactions involving group 6 Fischer carbene complexes: a source of inspiration for future catalytic transformations [J].

Angel Fernandez-Rodriguez, Manuel ;

Garcia-Garcia, Patricia ;

Aguilar, Enrique .

CHEMICAL COMMUNICATIONS, 2010, 46 (41) :7670-7687

[2]

[Anonymous], 1999, TETRAHEDRON LETT, V40, P3635

[3] PENTACARBONYLMETHYL(METHYLAMINO)CARBENECHROMIUM [J].

BAIKIE, PE ;

FISCHER, EO ;

MILLS, OS .

CHEMICAL COMMUNICATIONS, 1967, (23) :1199-&

[4] Group 6 Fischer carbene complexes:: "chemical multitalents" for multi-component reactions [J].

Barluenga, J ;

Fernández-Rodríguez, MA ;

Aguilar, E .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (03) :539-587

[5] Synthesis of heterocycles via group VI Fischer carbene complexes [J].

Barluenga, J ;

Santamaría, J ;

Tomás, M .

CHEMICAL REVIEWS, 2004, 104 (05) :2259-2283

[6] First intermolecular cyclopropanation of Fischer dialkylaminocarbene complexes.: Synthesis of 1-aminocyclopropanecarboxylic acid derivatives [J].

Barluenga, J ;

Aznar, F ;

Gutiérrez, I ;

García-Granda, S ;

Llorca-Baragaño, MA .

ORGANIC LETTERS, 2002, 4 (24) :4273-4276

[7] Intramolecular additions of various π-nucleophiles to chemoselectively activated amides and application to the synthesis of (±)-tashiromine [J].

Bélanger, G ;

Larouche-Gauthier, R ;

Ménard, F ;

Nantel, M ;

Barabé, F .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (02) :704-712

[8] Addition of tethered nonaromatic carbon nucleophiles to chemoselectively activated amides [J].

Bélanger, G ;

Larouche-Gauthier, R ;

Ménard, F ;

Nantel, M ;

Barabé, F .

ORGANIC LETTERS, 2005, 7 (20) :4431-4434

[9] Highly chemoselective formation of aldehyde enamines under very mild reaction conditions [J].

Belanger, Guillaume ;

Dore, Michael ;

Menard, Frederic ;

Darsigny, Veronique .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (19) :7481-7484

[10] Rapid Assembly of Quinolizidines via Consecutive Nucleophilic Cyclizations onto Activated Amides [J].

Belanger, Guillaume ;

O'Brien, Gary ;

Larouche-Gauthier, Robin .

ORGANIC LETTERS, 2011, 13 (16) :4268-4271

← 1 2 3 4 5 →