Gold-catalyzed heterocyclizations in alkynyl- and allenyl-β-lactams

被引:20
作者
Alcaide, Benito [1 ]
Almendros, Pedro [2 ]
机构
[1] Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, Grp Lactamas & Heterociclos Bioactivos,Unidad Aso, E-28040 Madrid, Spain
[2] CSIC, IQOG, E-28006 Madrid, Spain
来源
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 7卷
关键词
alkynes; allenes; gold; heterocyclizations; beta-lactams; GAMMA-ALLENOLS; REGIOSELECTIVITY CONTROL; ALPHA-HYDROXYALLENES; CARBON-HETEROATOM; BUILDING-BLOCKS; CYCLIZATION; CYCLOISOMERIZATION; HYDROALKOXYLATION; DERIVATIVES; IRON;
D O I
10.3762/bjoc.7.73
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New gold-catalyzed methods using the beta-lactam scaffold have been recently developed for the synthesis of different sized hetero-cycles. This overview focuses on heterocyclization reactions of allenic and alkynic beta-lactams which rely on the activation of the allene and alkyne component. The mechanism as well as the regio- and stereoselectivity of the cyclizations are also discussed.
引用
收藏
页码:622 / 630
页数:9
相关论文
共 66 条
[1]   β-lactams as versatile synthetic intermediates for the preparation of heterocycles of biological interest [J].
Alcaide, B ;
Almendros, P .
CURRENT MEDICINAL CHEMISTRY, 2004, 11 (14) :1921-1949
[2]   Recent advances in the stereocontrolled synthesis of bi- and tricyclic-β-lactams with non-classical structure [J].
Alcaide, B ;
Almendros, P .
CURRENT ORGANIC CHEMISTRY, 2002, 6 (03) :245-264
[3]  
Alcaide B, 2002, SYNLETT, P381
[4]   4-Oxoazetidine-2-carbaldehydes as useful building blocks in stereocontrolled synthesis [J].
Alcaide, B ;
Almendros, P .
CHEMICAL SOCIETY REVIEWS, 2001, 30 (04) :226-240
[5]   Chemodivergence in alkene/allene cycloetherification of enallenols: Iron versus noble metal catalysis [J].
Alcaide, Benito ;
Almendros, Pedro ;
Martinez del Campo, Teresa .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (26) :7756-7759
[6]   Metal-catalyzed regiodivergent cyclization of γ-allenols:: Tetrahydrofurans versus oxepanes [J].
Alcaide, Benito ;
Almendros, Pedro ;
del Campo, Teresa Martinez .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (35) :6684-6687
[7]   β-lactams:: Versatile building blocks for the stereoselective synthesis of non-β-lactam products [J].
Alcaide, Benito ;
Almendros, Pedro ;
Aragoncillo, Cristina .
CHEMICAL REVIEWS, 2007, 107 (11) :4437-4492
[8]   Straightforward Synthesis of Bridged Azaoxa Skeletons: Gold-Catalyzed Aminoketalization of Garner's Aldehyde-Derived Alkynes [J].
Alcaide, Benito ;
Almendros, Pedro ;
Carrascosa, Rocio .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (18) :4968-4971
[9]   Metal-Catalyzed Cycloisomerization and Tandem Oxycyclization/Hydroxylation of Alkynols: Synthesis of Nonfused, Spiranic and Fused Oxabicyclic β-Lactams [J].
Alcaide, Benito ;
Almendros, Pedro ;
Martinez del Campo, Teresa ;
Carrascosa, Rocio .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (25) :4912-4919
[10]   Gold/Acid-Cocatalyzed Regiodivergent Preparation of Bridged Ketals via Direct Bis-Oxycyclization of Alkynic Acetonides [J].
Alcaide, Benito ;
Almendros, Pedro ;
Carrascosa, Rocio ;
Rosario Torres, M. .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (08) :1277-1283