Gold-catalyzed oxycyclization of allenic carbamates: expeditious synthesis of 1,3-oxazin-2-ones

被引:31
作者
Alcaide, Benito [1 ]
Almendros, Pedro [2 ]
Teresa Quiros, M. [1 ]
Fernandez, Israel [3 ]
机构
[1] Univ Complutense Madrid, Fac Quim, CSIC,Dept Quim Organ 1, Unidad Asociada,Grp Lactamas & Heterociclos Bioac, E-28040 Madrid, Spain
[2] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
[3] Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
关键词
allenes; computational chemistry; gold; gold catalysis; heterocycles; reaction mechanisms; THERMODYNAMICALLY FAVORED ISOMERS; TERT-BUTYL CARBONATES; HYBRID MOLECULES; CYCLIZATION; ISOMERIZATION; PRODUCT; ALKYNES; ACCESS; SEMISYNTHESIS; DERIVATIVES;
D O I
10.3762/bjoc.9.93
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A combined experimental and computational study on regioselective gold-catalyzed synthetic routes to 1,3-oxazinan-2-ones (kinetically controlled products) and 1,3-oxazin-2-one derivatives (thermodynamically favored) from easily accessible allenic carbamates has been carried out.
引用
收藏
页码:818 / 826
页数:9
相关论文
共 76 条
[21]   EFFICIENT HOMOLOGATION OF ACETYLENES TO ALLENES [J].
CRABBE, P ;
FILLION, H ;
ANDRE, D ;
LUCHE, JL .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (19) :859-860
[22]   Hybrid Molecules Incorporating Natural Products: Applications in Cancer Therapy, Neurodegenerative Disorders and Beyond [J].
Decker, M. .
CURRENT MEDICINAL CHEMISTRY, 2011, 18 (10) :1464-1475
[23]   The Interplay between Mutasynthesis and Semisynthesis: Generation and Evaluation of an Ansamitocin Library [J].
Eichner, Simone ;
Knobloch, Tobias ;
Floss, Heinz G. ;
Fohrer, Joerg ;
Harmrolfs, Kirsten ;
Hermane, Jekaterina ;
Schulz, Anne ;
Sasse, Florenz ;
Spiteller, Peter ;
Taft, Florian ;
Kirschning, Andreas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (03) :752-757
[24]   A novel pathway for maytansinoid release from thioether linked antibody-drug conjugates (ADCs) under oxidative conditions [J].
Fishkin, Nathan ;
Maloney, Erin K. ;
Chari, Ravi V. J. ;
Singh, Rajeeva .
CHEMICAL COMMUNICATIONS, 2011, 47 (38) :10752-10754
[25]  
Hashmi A. S. K., 2012, MODERN GOLD CATALYZE
[26]   Gold-catalyzed organic reactions [J].
Hashmi, A. Stephen K. .
CHEMICAL REVIEWS, 2007, 107 (07) :3180-3211
[27]   Gold catalysis [J].
Hashmi, A. Stephen K. ;
Hutchings, Graham J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (47) :7896-7936
[28]   Gold Catalysis: 1,3-Oxazines by Cyclisation of Allene Amides [J].
Hashmi, A. Stephen K. ;
Schuster, Andreas M. ;
Litters, Sebastian ;
Rominger, Frank ;
Pernpointner, Markus .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (20) :5661-5667
[29]   Homogeneous Gold Catalysis Beyond Assumptions and Proposals-Characterized Intermediates [J].
Hashmi, A. Stephen K. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (31) :5232-5241
[30]  
Hashmi ASK, 2000, ANGEW CHEM INT EDIT, V39, P3590