Phosphine-Catalyzed Asymmetric (3+2) Annulations of δ-Acetoxy Allenoates with β-Carbonyl Amides: Enantioselective Synthesis of Spirocyclic β-Keto γ-Lactams

被引：56
作者：
Ni, Chunjie [1 ]
Chen, Jiangfei [1 ]
Zhang, Yuwen [1 ]
Hou, Yading [1 ]
Wang, Dong [1 ]
Tong, Xiaofeng [1 ]
Zhu, Shou-Fei [2 ,3 ]
Zhou, Qi-Lin [2 ,3 ]
机构：
[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, 1 Gehu Rd, Changzhou 213164, Peoples R China
[2] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
[3] Nankai Univ, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 13期
基金：
中国国家自然科学基金;
关键词：
HIGHLY FUNCTIONALIZED TETRAHYDROPYRIDINES; QUATERNARY STEREOCENTERS; CYCLOADDITION REACTIONS; DOMINO REACTIONS; FACILE ACCESS; ALLENES; ESTERS; ACID; CONSTRUCTION; HETEROCYCLES;
D O I：
10.1021/acs.orglett.7b01717
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
While the phosphine catalysis is a powerful tool for the construction of N-heterocycles, the phosphine-catalyzed annulations toward lactam motif are still extremely scarce. Here, we report the asymmetric (3 + 2) annulations of delta-acetoxy allenoates with beta-carbonyl amides by using the (R)-SITCP catalyst. The delta C and gamma C of allenoate respectively engage in annulation with the alpha C and N of the amide, forging a gamma-lactam with good to excellent stereoselectivity.
引用
收藏
页码：3668 / 3671
页数：4
相关论文
共 69 条
[1]   Stereoselective DABCO-Catalyzed Synthesis of (E)-α-Ethynyl-α,β-Unsaturated Esters from Allenyl Acetates [J].
Choe, Yongsik ;
Lee, Phil Ho .
ORGANIC LETTERS, 2009, 11 (06) :1445-1448
[2]   Phosphine-Catalyzed Enantioselective Synthesis of Oxygen Heterocycles [J].
Chung, Ying Kit ;
Fu, Gregory C. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (12) :2225-2227
[3]   Enantioselective catalysis and complexity generation from allenoates [J].
Cowen, Bryan J. ;
Miller, Scott J. .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3102-3116
[4]   Efficient Highly Selective Synthesis of Methyl 2-(Ethynyl)alk-2(E)-enoates and 2-(1′-Chlorovinyl)alk-2(Z)-enoates from 2-(Methoxycarbonyl)-2,3-allenols [J].
Deng, Youqian ;
Jin, Xin ;
Fu, Chunling ;
Ma, Shengming .
ORGANIC LETTERS, 2009, 11 (10) :2169-2172
[5]   A Cooperative Participation of the Amido Group in the Organocatalytic Construction of All-Carbon Quaternary Stereocenters by Michael Addition with β-Ketoamides [J].
Duque, Maria del Mar Sanchez ;
Basle, Olivier ;
Isambert, Nicolas ;
Gaudel-Siri, Anouk ;
Genisson, Yves ;
Plaquevent, Jean-Christophe ;
Rodriguez, Jean ;
Constantieux, Thierry .
ORGANIC LETTERS, 2011, 13 (13) :3296-3299
[6]   Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs [J].
Fan, Yi Chiao ;
Kwon, Ohyun .
CHEMICAL COMMUNICATIONS, 2013, 49 (99) :11588-11619
[7]   Salinosporamide A:: A highly cytotoxic proteasome inhibitor from a novel microbial source, a marine bacterium of the new genus Salinospora [J].
Feling, RH ;
Buchanan, GO ;
Mincer, TJ ;
Kauffman, CA ;
Jensen, PR ;
Fenical, W .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (03) :355-+
[8]   Synthesis of 3,3′-Spirocyclic Oxindoles via Phosphine Catalyzed [4+2] Cyclizations [J].
Gicquel, Maxime ;
Gomez, Catherine ;
Retailleau, Pascal ;
Voituriez, Arnaud ;
Marinetti, Angela .
ORGANIC LETTERS, 2013, 15 (15) :4002-4005
[9]   Phosphine Organocatalysis in the Synthesis of Natural Products and Bioactive Compounds [J].
Gomez, Catherine ;
Betzer, Jean-Francois ;
Voituriez, Arnaud ;
Marinetti, Angela .
CHEMCATCHEM, 2013, 5 (05) :1055-1065
[10]   α,β-Unsaturated Acyl Cyanides as New Bis-Electrophiles for Enantioselective Organocatalyzed Formal [3+3]Spiroannulation [J].
Goudedranche, Sebastien ;
Bugaut, Xavier ;
Constantieux, Thierry ;
Bonne, Damien ;
Rodriguez, Jean .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (02) :410-415
1234567