Stereoselective intramolecular cyclopropanation through catalytic olefin activation

被引:63
作者
Huang, Xueliang [1 ]
Klimczyk, Sebastian [1 ]
Veiros, Luis F. [2 ]
Maulide, Nuno [1 ]
机构
[1] Max Planck Inst Kohlenforsch, Mulheim, Germany
[2] Univ Tecn Lisboa, Ctr Quim Estrutural, Inst Super Tecn, P-1049001 Lisbon, Portugal
关键词
ALPHA-AMINO-ACIDS; OXIDATIVE CYCLIZATION; UNACTIVATED ALKENES; NATURAL OCCURRENCE; EFFICIENT ACCESS; CARBENE-TRANSFER; GOLD; HYDROAMINATION; CYCLOISOMERIZATION; COMPLEXES;
D O I
10.1039/c2sc21914j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel stereoselective and convergent catalytic method for the cyclopropanation of electron-neutral and -rich olefins by sulfonium ylides is reported which unusually proceeds through olefin activation rather than by metal carbene formation.
引用
收藏
页码:1105 / 1110
页数:6
相关论文
共 96 条
[1]   Catalytic, asymmetric sulfur ylide-mediated epoxidation of carbonyl compounds: Scope, selectivity, and applications in synthesis [J].
Aggarwal, VK ;
Winn, CL .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :611-620
[2]   Alternative synthetic methods through new developments in catalysis by gold [J].
Arcadi, Antonio .
CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325
[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]   Room temperature hydroamination of N-alkenyl ureas catalyzed by a gold(I) N-heterocyclic carbene complex [J].
Bender, Christopher F. ;
Widenhoefer, Ross A. .
ORGANIC LETTERS, 2006, 8 (23) :5303-5305
[5]   Gold(I)-catalyzed intramolecular hydroamination of unactivated alkenes with carboxamides [J].
Bender, Christopher F. ;
Widenhoefer, Ross A. .
CHEMICAL COMMUNICATIONS, 2006, (39) :4143-4144
[6]   On the Impact of Steric and Electronic Properties of Ligands on Gold(I)-Catalyzed Cycloaddition Reactions [J].
Benitez, Diego ;
Tkatchouk, Ekaterina ;
Gonzalez, Ana Z. ;
Goddard, William A., III ;
Toste, F. Dean .
ORGANIC LETTERS, 2009, 11 (21) :4798-4801
[7]  
Benitez D, 2009, NAT CHEM, V1, P482, DOI [10.1038/NCHEM.331, 10.1038/nchem.331]
[8]   Gold-Catalyzed Oxidative Cyclizations of cis-3-En-1-ynes To Form Cyclopentenone Derivatives [J].
Bhunia, Sabyasachi ;
Ghorpade, Satish ;
Huple, Deepak B. ;
Liu, Rai-Shung .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (12) :2939-2942
[9]   Natural occurrence, syntheses, and applications of cyclopropyl-group-containing α-amino acids.: 2.: 3,4- and 4,5-methanoamino acids [J].
Brackmann, Farina ;
de Meijere, Armin .
CHEMICAL REVIEWS, 2007, 107 (11) :4538-4583
[10]   Natural occurrence, syntheses, and applications of cyclopropyl-group-containing α-amino acids.: 1.: 1-aminocyclopropanecarboxylic acid and other 2,3-methanoamino acids [J].
Brackmann, Farina ;
de Meijere, Armin .
CHEMICAL REVIEWS, 2007, 107 (11) :4493-4537