Rhodium-Catalyzed Domino Conjugate Addition-Cyclization Reactions for the Synthesis of a Variety of N- and O-Heterocycles: Arylboroxines as Effective Carbon Nucleophiles

被引：35

作者：

Park, Ja Ock ^{[2
]}

Youn, So Won ^{[1
]}

机构：

[1] Hanyang Univ, Dept Chem, Seoul 133791, South Korea

[2] Pukyong Natl Univ, Dept Chem, Pusan 608737, South Korea

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 10期

关键词：

PICTET-SPENGLER REACTION; SEQUENTIAL C-C; ASYMMETRIC 1,4-ADDITION; ENANTIOSELECTIVE SYNTHESIS; ALKENYLBORONIC ACIDS; FACILE CONSTRUCTION; BOND FORMATIONS; REAGENTS; PHENOLS; DIENES;

D O I：

10.1021/ol100610v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Facile and efficient Rh(I)-catalyzed domino conjugate addition-cyclization reactions of olefins bearing two electrophilic sites and a pendant nucleophile with organoboroxines have been developed to afford a variety of N- and O-heterocycles, such as 3,4-dihydroquinolin-2(1H)-ones, 3,4-dihydrocoumarins, and pyrrolidin-2-ones, which constitute important motifs in biologically active natural and synthetic organic compounds.

引用

页码：2258 / 2261

页数：4

共 45 条

[1] N,N-Diethyl O-Carbamate: Directed Metalation Group and Orthogonal Suzuki-Miyaura Cross-Coupling Partner [J].

Antoft-Finch, Aurora ;

Blackburn, Tom ;

Snieckus, Victor .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (49) :17750-17752

[2] Enantioselective syntheses of (-)-(R)-rolipram, (-)-(R)-baclofen and other GABA analogues via rhodium-catalyzed conjugate addition of arylboronic acids [J].

Becht, JM ;

Meyer, O ;

Helmchen, G .

SYNTHESIS-STUTTGART, 2003, (18) :2805-2810

[3] Palladium-Catalyzed Reaction of Arenediazonium Tetrafluoroborates with Methyl 4-Hydroxy-2-butenoate: An Approach to 4-Aryl Butenolides and an Expeditious Synthesis of Rubrolide E [J].

Cacchi, Sandro ;

Fabrizi, Giancarlo ;

Goggiamani, Antonella ;

Sferrazza, Alessio .

SYNLETT, 2009, (08) :1277-1280

[4] High performance of a chiral diene-rhodium catalyst for the asymmetric 1,4-addition of arylboroxines to α,β-unsaturated ketones [J].

Chen, FX ;

Kina, A ;

Hayashi, T .

ORGANIC LETTERS, 2006, 8 (02) :341-344

[5] Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins: Asymmetric synthesis of (R)-tolterodine [J].

Chen, G ;

Tokunaga, N ;

Hayashi, T .

ORGANIC LETTERS, 2005, 7 (11) :2285-2288

[6] Stereoselectivity control in the Rh(I)-catalyzed conjugate additions of aryl and alkenylboronic acids to unprotected hydroxycyclopentenones [J].

de la Herrán, G ;

Mba, M ;

Murcia, MC ;

Plumet, J ;

Csáky, AG .

ORGANIC LETTERS, 2005, 7 (08) :1669-1671

[7]

Donnelly D.M.X., 1986, FLAVONOIDS ADV RES 1, P239

[8] Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds [J].

Fagnou, K ;

Lautens, M .

CHEMICAL REVIEWS, 2003, 103 (01) :169-196

[9] New synthesis of biaryls via Rh-catalyzed decarbonylative Suzuki-coupling of carboxylic anhydrides with arylboroxines [J].

Goossen, LJ ;

Paetzold, J .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1665-1668

[10] Catalytic asymmetric tandem transformations triggered by conjugate additions [J].

Guo, HC ;

Ma, JA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (03) :354-366

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