Synthesis of Functionalized Polycyclic Compounds: Rhodium(I)-Catalyzed Intramolecular Cycloaddition of Yne and Ene Vinylidenecyclopropanes

被引:34
作者
Lu, Bei-Li [1 ]
Shi, Min [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
cycloadditions; C?H bond activation; heterocycles; rhodium; synthetic methods; C-H ACTIVATION; SUBSTITUTED RHODIUM CARBENOIDS; ACID CATALYZED REACTION; BOND ACTIVATION; LEWIS-ACID; ORGANIC-SYNTHESIS; VINYLIDENE-CYCLOPROPANES; DERIVATIVES; REARRANGEMENT; CYCLIZATION;
D O I
10.1002/anie.201105292
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Three ring circus: The title reaction can efficiently provide functionalized polycyclic compounds containing cyclobutene (see scheme; PG=protecting group) or aza-cyclooctene moieties in a highly regio- and diastereoselective manner with moderate to good yields under mild reaction conditions. The scope and limitations are disclosed and plausible reaction mechanisms are discussed. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:12027 / 12031
页数:5
相关论文
共 78 条
[1]   Exploiting [2+2] cycloaddition chemistry: achievements with allenes [J].
Alcaide, Benito ;
Almendros, Pedro ;
Aragoncillo, Cristina .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :783-816
[2]   A FLEXIBLE ROUTE TO 1-BROMO-2-ALKYLCYCLOPROPENES [J].
ALDULAYYNI, AR ;
BAIRD, MS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (12) :1547-1548
[3]   Transition Metal Catalyzed Cycloisomerizations of 1,n-Allenynes and -Allenenes [J].
Aubert, Corinne ;
Fensterbank, Louis ;
Garcia, Pierre ;
Malacria, Max ;
Simonneau, Antoine .
CHEMICAL REVIEWS, 2011, 111 (03) :1954-1993
[4]   Rhodium(I)-catalyzed ene-allene carbocyclization strategy for the formation of azepines and oxepines [J].
Brummond, KM ;
Chen, HF ;
Mitasev, B ;
Casarez, AD .
ORGANIC LETTERS, 2004, 6 (13) :2161-2163
[5]   Modulation of the hepatic alpha(1)-adrenoceptor responsiveness by colchicine: Dissociation of free cytosolic Ca2+-dependent and independent responses [J].
Butta, N ;
MartinRequero, A ;
Urcelay, E ;
Parrilla, R ;
Ayuso, MS .
BRITISH JOURNAL OF PHARMACOLOGY, 1996, 118 (07) :1797-1805
[6]   Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].
Colby, Denise A. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
CHEMICAL REVIEWS, 2010, 110 (02) :624-655
[7]   Intermolecular C-H insertions of donor/acceptor-substituted rhodium carbenoids: A practical solution for catalytic enantioselective C-H activation [J].
Davies, HML ;
Loe, O .
SYNTHESIS-STUTTGART, 2004, (16) :2595-2608
[8]   Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion [J].
Davies, HML ;
Beckwith, REJ .
CHEMICAL REVIEWS, 2003, 103 (08) :2861-2903
[9]   Catalytic and enantioselective allylic C-H activation with donor-acceptor-substituted carbenoids [J].
Davies, HML ;
Nikolai, J .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (23) :4176-4187
[10]   Enantioselective double C-H activation of dihydronaphthalenes [J].
Davies, HML ;
Jin, QH .
ORGANIC LETTERS, 2005, 7 (12) :2293-2296