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
[1]  
Buchanan GS, 2010, CURR ORG SYNTH, V7, P363
[2]   Palladium-Catalyzed Insertion of CO2 into Vinylaziridines: New Route to 5-Vinyloxazolidinones [J].
Fontana, Francesco ;
Chen, C. Chun ;
Aggarwal, Varinder K. .
ORGANIC LETTERS, 2011, 13 (13) :3454-3457
[3]   Development of a stepwise [3+3] annelation to functionalized piperidines [J].
Goodenough, KM ;
Raubo, P ;
Harrity, JPA .
ORGANIC LETTERS, 2005, 7 (14) :2993-2996
[4]   [3+3] cycloadditions and related strategies in alkaloid natural product synthesis [J].
Harrity, JPA ;
Provoost, O .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (08) :1349-1358
[5]   Development of a [3+3] cycloaddition strategy toward functionalized piperidines [J].
Hedley, SJ ;
Moran, WJ ;
Price, DA ;
Harrity, JPA .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4286-4292
[6]   A formal [3+3] cycloaddition approach to natural-product synthesis [J].
Hsung, RP ;
Kurdyumov, AV ;
Sydorenko, N .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (01) :23-44
[7]   Design, synthesis, and structure-activity relationships of novel spiro-piperidines as acetyl-CoA carboxylase inhibitors [J].
Kamata, Makoto ;
Yamashita, Tohru ;
Kina, Asato ;
Funata, Masaaki ;
Mizukami, Atsushi ;
Sasaki, Masako ;
Tani, Akiyoshi ;
Funami, Miyuki ;
Amano, Nobuyuki ;
Fukatsu, Kohji .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (11) :3643-3647
[8]  
Kimura M., 2008, Angew. Chem., Int. Ed., V120, P5887
[9]   Convenient synthesis of pyrrolidines by amphiphilic allylation of imines with 2-methylenepropane-1,3-diols [J].
Kimura, Masanari ;
Tamaki, Takato ;
Nakata, Masanori ;
Tohyama, Katsumi ;
Tamaru, Yoshinao .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (31) :5803-5805
[10]   Asymmetric allylation of unsymmetrical 1,3-diketones using a BINAP-palladium catalyst [J].
Kuwano, R ;
Uchida, K ;
Ito, Y .
ORGANIC LETTERS, 2003, 5 (12) :2177-2179