Nontraditional Reactions of Azomethine Ylides: Decarboxylative Three-Component Couplings of α-Amino Acids

被引:203
作者
Zhang, Chen [1 ]
Seidel, Daniel [1 ]
机构
[1] Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA
基金
美国国家科学基金会;
关键词
C-H BOND; ORGANIC-SYNTHESIS; REDOX PROCESS; ISOMERIZATION; NITROGEN; ROUTE; TRANSAMINATION; CYCLOADDITIONS; HETEROCYCLES; MECHANISM;
D O I
10.1021/ja910719x
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
New reactions of azomethine ylides with nontraditional dipolarophiles are reported. Azomethine ylides, formed ill situ via decarboxylative condensations of alpha-amino acids with aldehydes, Undergo reactions with naphthols, indoles, alkynes, and nitroalkanes.
引用
收藏
页码:1798 / +
页数:3
相关论文
共 46 条
[1]   1,7-electrocyclisation of non-stabilised α,β:γ,δ-unsaturated azomethine ylides [J].
Arany, A ;
Bendell, D ;
Groundwater, PW ;
Garnett, I ;
Nyerges, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (18) :2605-2608
[2]   IMINIUM ION ROUTE TO AZOMETHINE YLIDES FROM PRIMARY AND SECONDARY-AMINES [J].
ARDILL, H ;
GRIGG, R ;
SRIDHARAN, V ;
SURENDRAKUMAR, S ;
THIANPATANAGUL, S ;
KANAJUN, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (08) :602-604
[3]   Aldehyde- and Ketone-Induced Tandem Decarboxylation-Coupling (Csp3-Csp) of Natural α-Amino Acids and Alkynes [J].
Bi, Hai-Peng ;
Teng, Qingfeng ;
Guan, Min ;
Chen, Wen-Wen ;
Liang, Yong-Min ;
Yao, Xiaojun ;
Li, Chao-Jun .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (03) :783-788
[4]   A Novel Iron-Catalyzed Decarboxylative Csp3-Csp2 Coupling of Proline Derivatives and Naphthol [J].
Bi, Hai-Peng ;
Chen, Wen-Wen ;
Liang, Yong-Min ;
Li, Chao-Jun .
ORGANIC LETTERS, 2009, 11 (15) :3246-3249
[5]   The Copper-Catalyzed Decarboxylative Coupling of the sp3-Hybridized Carbon Atoms of α-Amino Acids [J].
Bi, Hai-Peng ;
Zhao, Liang ;
Liang, Yong-Min ;
Li, Chao-Jun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (04) :792-795
[6]   Redox Economy in Organic Synthesis [J].
Burns, Noah Z. ;
Baran, Phil S. ;
Hoffmann, Reinhard W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (16) :2854-2867
[7]   Direct sp3 C-H bond activation adjacent to nitrogen in heterocycles [J].
Campos, Kevin R. .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1069-1084
[8]   NOVEL STERICALLY MEDIATED TRANSFORMATION OF PROLINE [J].
COHEN, N ;
BLOUNT, JF ;
LOPRESTI, RJ ;
TRULLINGER, DP .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (22) :4005-4007
[9]   Intramolecular dipolar cycloaddition reactions of azomethine ylides [J].
Coldham, I ;
Hufton, R .
CHEMICAL REVIEWS, 2005, 105 (07) :2765-2809
[10]   Intramolecular Hydro-N-alkylation of Hydrazones and Oxime Ethers: Synthesis of Novel D-Secoestrone Isoquinuclidines via Domino 1,5-Hydride Shift/Cyclization [J].
Frank, Eva ;
Schneider, Gyula ;
Kadar, Zalan ;
Woelfling, Janos .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (21) :3544-3553