A Pd-Catalyzed Synthesis of Functionalized Piperidines

被引:30
作者
Allen, Benjamin D. W. [1 ]
Connolly, Matthew J. [1 ]
Harrity, Joseph P. A. [1 ]
机构
[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England
基金
英国工程与自然科学研究理事会;
关键词
annulation; enantioselectivity; Pd catalysis; piperidine; NATURAL-PRODUCT SYNTHESIS; 3+3 ANNELATION; CYCLOADDITION; TRIMETHYLENEMETHANE; HETEROCYCLES; ANNULATIONS; ALLYLATION; STRATEGY; IMINES; ROUTE;
D O I
10.1002/chem.201602586
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A readily available cyclic carbamate 1 functions as a general precursor to a range of functionalized piperidine products via a new Pd-catalyzed annulation strategy. An asymmetric catalytic variant provides a rapid and efficient means to access these heterocycles with high to excellent levels of enantiocontrol. Finally, these richly functionalized compounds are amenable to further chemoselective elaboration.
引用
收藏
页码:12999 / 13003
页数:5
相关论文
共 26 条
[11]   Transition metal-mediated cycloaddition reactions [J].
Lautens, M ;
Klute, W ;
Tam, W .
CHEMICAL REVIEWS, 1996, 96 (01) :49-92
[12]  
Lowe M. A., 2011, ANGEW CHEM, V123, P6494
[13]   Palladium-Mediated Annulation of Vinyl Aziridines with Michael Acceptors: Stereocontrolled Synthesis of Substituted Pyrrolidines and Its Application in a Formal Synthesis of (-)-α-Kainic Acid [J].
Lowe, Martin A. ;
Ostovar, Mehrnoosh ;
Ferrini, Serena ;
Chen, C. Chun ;
Lawrence, Paul G. ;
Fontana, Francesco ;
Calabrese, Andrew A. ;
Aggarwal, Varinder K. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (28) :6370-6374
[14]   A Mild and Regioselective Route to Functionalized Quinazolines [J].
Maiden, Tracy M. M. ;
Swanson, Stephen ;
Procopiou, Panayiotis A. ;
Harrity, Joseph P. A. .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (41) :14342-14346
[15]   A [3+3] annelation approach to tetrahydropyridines [J].
Pattenden, Lisa C. ;
Wybrow, Robert A. J. ;
Smith, Stephen A. ;
Harrity, Joseph P. A. .
ORGANIC LETTERS, 2006, 8 (14) :3089-3091
[16]   The impact of aromatic ring count on compound developability - are too many aromatic rings a liability in drug design? [J].
Ritchie, Timothy J. ;
Macdonald, Simon J. F. .
DRUG DISCOVERY TODAY, 2009, 14 (21-22) :1011-1020
[17]   New ring-opening polymerization via a π-allylpalladium complex.: 5.: Multibranching polymerization of cyclic carbamate to produce hyperbranched dendritic polyamine [J].
Suzuki, M ;
Yoshida, S ;
Shiraga, K ;
Saegusa, T .
MACROMOLECULES, 1998, 31 (06) :1716-1719
[18]  
Trost B.M., 1986, Angew. Chem, V98, P1
[19]   NEW CONJUNCTIVE REAGENTS - 2-ACETOXYMETHYL-3-ALLYLTRIMETHYLSILANE FOR METHYLENECYCLOPENTANE ANNULATIONS CATALYZED BY PALLADIUM(0) [J].
TROST, BM ;
CHAN, DMT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (21) :6429-6432
[20]   A [3+2] AND [4+3] CYCLOADDITION APPROACH TO N-HETEROCYCLES VIA PD-CATALYZED TMM REACTIONS WITH IMINES [J].
TROST, BM ;
MARRS, CM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :6636-6645