Rhodium-Catalyzed Cascade Reactions of Dienynes Leading to Substituted Dihydronaphthalenes and Naphthalenes

被引：23

作者：

Okazaki, Eri ^{[1
]}

Okamoto, Ryuichi ^{[1
]}

Shibata, Yu ^{[1
]}

Noguchi, Keiichi ^{[2
]}

Tanaka, Ken ^{[1
]}

机构：

[1] Tokyo Univ Agr & Technol, Dept Appl Chem, Grad Sch Engn, Koganei, Tokyo 1848588, Japan

[2] Tokyo Univ Agr & Technol, Instrumentat Anal Ctr, Koganei, Tokyo 1848588, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 27期

关键词：

carbonyl ene reactions; cascade reactions; cycloisomerizations; dienynes; rhodium; 2+2+2 CYCLOADDITION STRATEGY; AMINO-CLAISEN REARRANGEMENT; INTERMOLECULAR HYDROACYLATION; ASYMMETRIC ISOMERIZATION; INTRAMOLECULAR HYDROACYLATION; ALKENYL ISOCYANATES; GRUBBS CATALYST; DIALLYL-ETHERS; TANDEM; ALDEHYDES;

D O I：

10.1002/anie.201202125

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Five in one: Catalytic cascade reactions of dienynes catalyzed by cationic rhodium(I)-binap complexes lead to the formation of 1,2-dihydronaphthalenes, naphthalenes, and 1,4-dihydronaphthalenes. These cascade reactions involve up to five fundamentally different transformations, including the catalytic enantioselective carboformylation of alkenes with aldehydes or the cycloisomerization of enallenes. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：6722 / 6727

页数：6

共 72 条

[1]

Ammar H. Ben, 2002, J ORGANOMET CHEM, V662, P63

[2]

[Anonymous], 2006, ANGEW CHEM

[3] Cascading pericyclic reactions: building complex carbon frameworks for natural product synthesis [J].

Arns, Steve ;

Barriault, Louis .

CHEMICAL COMMUNICATIONS, 2007, (22) :2211-2221

[4] Functionalised allylsilanes from silylcopper reagents and allene.: A useful strategy for cyclopentane annulations [J].

Barbero, A ;

García, C ;

Pulido, FJ .

TETRAHEDRON, 2000, 56 (18) :2739-2751

[5] ASYMMETRIC CATALYSIS - ASYMMETRIC CATALYTIC INTRAMOLECULAR HYDROACYLATION OF 4-PENTENALS USING CHIRAL RHODIUM DIPHOSPHINE CATALYSTS [J].

BARNHART, RW ;

WANG, XQ ;

NOHEDA, P ;

BERGENS, SH ;

WHELAN, J ;

BOSNICH, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (05) :1821-1830

[6] HOMOGENEOUS CATALYSIS - CATALYTIC PRODUCTION OF SIMPLE ENOLS [J].

BERGENS, SH ;

BOSNICH, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) :958-967

[7] Palladium catalysed queuing processes. Part 1: Termolecular cyclization-anion capture employing carbon monoxide as a relay switch and hydride, organotin(IV) or boron reagents [J].

Brown, S ;

Clarkson, S ;

Grigg, R ;

Thomas, WA ;

Sridharan, V ;

Wilson, DM .

TETRAHEDRON, 2001, 57 (07) :1347-1359

[8] Tandem and domino catalytic strategies for enantioselective synthesis [J].

Chapman, Christopher J. ;

Frost, Christopher G. .

SYNTHESIS-STUTTGART, 2007, (01) :1-21

[9] Regio- and Enantioselective Intermolecular Hydroacylation: Substrate-Directed Addition of Salicylaldehydes to Homoallylic Sulfides [J].

Coulter, Matthew M. ;

Kou, Kevin G. M. ;

Galligan, Baye ;

Dong, Vy M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (46) :16330-16333

[10] Rh-Catalyzed Intramolecular Olefin Hydroacylation: Enantioselective Synthesis of Seven- and Eight-Membered Heterocycles [J].

Coulter, Matthew M. ;

Dornan, Peter K. ;

Dong, Vy M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (20) :6932-+

← 1 2 3 4 5 6 7 8 →