Application of a Rhodium-Catalyzed Addition/Cyclization Sequence toward the Synthesis of Polycyclic Heteroaromatics

被引：32

作者：

Tseng, Nai-Wen ^{[1
]}

Lautens, Mark ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 04期

基金：

加拿大自然科学与工程研究理事会;

关键词：

TANDEM CONJUGATE ADDITION; RING-OPENING REACTIONS; ETHYL CYCLOPROPYLIDENEACETATE; ARYLBORONATE ESTERS; CYCLIZATION; CYCLOADDITION; DERIVATIVES; PALLADIUM; ALKENES; ALKYNES;

D O I：

10.1021/jo802622d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A cascade rhodium-catalyzed addition/cyclization reaction of bifunctional heteroromatic boronate esters to strained bicyclic alkenes has been developed. This method provides an efficient route to generate a variety of polycyclic heteroaromatic molecules containing benzothiophene, benzofuran, and indole moieties.

引用

页码：1809 / 1811

页数：3

共 32 条

[1]

Brown T, 2006, TOP HETEROCYCLIC CHE, V2, P1, DOI 10.1007/7081_003

[2]

Evans PA, 2005, MODERN RHODIUM-CATALYZED ORGANIC REACTIONS, P1, DOI 10.1002/3527604693

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

Fagnou, K ;

Lautens, M .

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

[4] A novel palladium-mediated coupling approach to 2,3-disubstituted benzo[b]thiophenes and its application to the synthesis of tubulin binding agents [J].

Flynn, BL ;

Verdier-Pinard, P ;

Hamel, E .

ORGANIC LETTERS, 2001, 3 (05) :651-654

[5] Palladium-catalyzed [4+3] intramolecular cycloaddition of alkylidenecyclopropanes and dienes [J].

Gulias, Moises ;

Duran, Juan ;

Lopez, Fernando ;

Castedo, Luis ;

Mascarenas, Jose L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (36) :11026-+

[6] Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions [J].

Hayashi, T ;

Yamasaki, K .

CHEMICAL REVIEWS, 2003, 103 (08) :2829-2844

[7] ANTIESTROGENS .2. STRUCTURE ACTIVITY STUDIES IN A SERIES OF 3-AROYL-2-ARYLBENZO[B]THIOPHENE DERIVATIVES LEADING TO [6-HYDROXY-2-(4-HYDROXYPHENYL)BENZO[B]THIEN-3-YL][4-[2-(1-PIPERIDINYL)ETHOXY]-PHENYL]METHANONE HYDROCHLORIDE (LY156758), A REMARKABLY EFFECTIVE ESTROGEN ANTAGONIST WITH ONLY MINIMAL INTRINSIC ESTROGENICITYO[ [J].

JONES, CD ;

JEVNIKAR, MG ;

PIKE, AJ ;

PETERS, MK ;

BLACK, LJ ;

THOMPSON, AR ;

FALCONE, JF ;

CLEMENS, JA .

JOURNAL OF MEDICINAL CHEMISTRY, 1984, 27 (08) :1057-1066

[8]

KUNO A, 1996, Patent No. 9604241

[9] Rhodium-catalyzed tandem cyclization:: Formation of 1H-indenes and 1-alkylideneindans from arylboronate esters in aqueous media [J].

Lautens, M ;

Marquardt, T .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (14) :4607-4614

[10] Addition of bifunctional organoboron reagents to strained alkenes. Carbon-carbon bond formation with Rh(I) catalysis in aqueous media [J].

Lautens, M ;

Mancuso, J .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (10) :3478-3487

← 1 2 3 4 →