Rhodium-catalyzed one-pot synthesis of substituted pyridine derivatives from α,β-unsaturated ketoximes and alkynes

被引：276

作者：

Parthasarathy, Kanniyappan ^{[1
]}

Jeganmohan, Masilamani ^{[1
]}

Cheng, Chien-Hong ^{[1
]}

机构：

[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 02期

关键词：

D O I：

10.1021/ol7028367

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A rhodium-catalyzed chelation-assisted CA activation of alpha,beta-unsaturated ketoximes and the reaction with alkynes to afford highly substituted pyridine derivatives is described.

引用

页码：325 / 328

页数：4

共 46 条

[1] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[2] Water-soluble cyclopalladated aryl oxime: a potent 'green' catalyst [J].

Bezsoudnova, EY ;

Ryabov, AD .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 622 (1-2) :38-42

[3] Carbocyclization of aromatic iodides, bicyclic alkenes, and benzynes involving a palladium-catalyzed C-H bond activation as a key step [J].

Bhuvaneswari, Sivakolundu ;

Jeganmohan, Masilamani ;

Cheng, Chien-Hong .

ORGANIC LETTERS, 2006, 8 (24) :5581-5584

[4] INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS OF N-SULFONYL ALPHA,BETA-UNSATURATED IMINES - A GENERAL-APPROACH TO IMPLEMENTATION OF THE 4-PI PARTICIPATION OF 1-AZA-1,3-BUTADIENES IN DIELS-ALDER REACTIONS [J].

BOGER, DL ;

CORBETT, WL ;

CURRAN, TT ;

KASPER, AM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (05) :1713-1729

[5] Total synthesis of the rubrolone aglycon [J].

Boger, DL ;

Ichikawa, S ;

Jiang, HJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (49) :12169-12173

[6] INTRAMOLECULAR ADDITION OF VINYL AND ARYL RADICALS TO OXIME ETHERS IN THE SYNTHESIS OF 5-MEMBERED, 6-MEMBERED AND 7-MEMBERED RING-SYSTEMS [J].

BOOTH, SE ;

JENKINS, PR ;

SWAIN, CJ ;

SWEENEY, JB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (23) :3499-3508

[7] α,β-Unsaturated imines from titanium hydroamination and functionalization by rhodium C-H activation [J].

Cao, CS ;

Li, YH ;

Shi, YH ;

Odom, AL .

CHEMICAL COMMUNICATIONS, 2004, (17) :2002-2003

[8] Cobalt-catalyzed diastereoselective reductive [3+2] cycloaddition of allenes and enones [J].

Chang, Hong-Tai ;

Jayanth, Thiruvellore Thatai ;

Cheng, Chien-Hong .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (14) :4166-+

[9] Ruthenium-catalyzed reaction of α,β-unsaturated imines with carbon monoxide and alkenes leading to β,γ-unsaturated γ-butyrolactams:: Involvement of direct carbonylation at olefinic C-H bonds as a key step [J].

Chatani, N ;

Kamitani, A ;

Murai, S .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :7014-7018

[10] Stereoselective alkylation of α,β-unsaturated imines via C-H bond activation [J].

Colby, DA ;

Bergman, RG ;

Ellman, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (17) :5604-5605

← 1 2 3 4 5 →