Synthesis of novel and uniquely shaped 3-azabicyclo[4.2.0]octan-4-one derivatives by sequential Ugi/[2+2] ene-enone photocycloadditions

被引:32
作者
Akritopoulou-Zanze, Irini [1 ]
Whitehead, Alan [1 ]
Waters, Jan E. [1 ]
Henry, Rodger F. [1 ]
Djuric, Stevan W. [1 ]
机构
[1] Abbott Labs, Scaffold Oriented Synth & Struct Chem, Abbott Pk, IL 60064 USA
关键词
MULTICOMPONENT REACTIONS; UGI REACTION; ISOCYANIDE; ACCESS;
D O I
10.1021/ol070164l
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report a new methodology for the construction of novel and uniquely shaped 3-azabicyclo[4.2.0]octan-4-one derivatives by combining the Ugi multicomponent reaction with [2+2] enone-olefin photochemical transformations. The overall sequence is capable of creating up to five stereocenters; however, in most cases, only two diastereomers are observed.
引用
收藏
页码:1299 / 1302
页数:4
相关论文
共 24 条
[1]   A versatile synthesis of fused triazolo derivatives by sequential Ugi/alkyne-azide cycloaddition reactions [J].
Akritopoulou-Zanze, I ;
Gracias, V ;
Djuric, SW .
TETRAHEDRON LETTERS, 2004, 45 (46) :8439-8441
[2]   Synthesis of novel fused isoxazoles and isoxazolines by sequential Ugi/INOC reactions [J].
Akritopoulou-Zanze, I ;
Gracias, V ;
Moore, JD ;
Djuric, SW .
TETRAHEDRON LETTERS, 2004, 45 (17) :3421-3423
[3]  
[Anonymous], MOL SUPRAM PHOTOCHEM
[4]   Stereoselective intra- and intermolecular [2+2] photocycloaddition reactions of 4-(2'-aminoethyl)quinolones [J].
Brandes, S ;
Selig, P ;
Bach, T .
SYNLETT, 2004, (14) :2588-2590
[5]   SYNTHETIC APPLICATIONS OF INTRAMOLECULAR ENONE OLEFIN PHOTOCYCLOADDITIONS [J].
CRIMMINS, MT .
CHEMICAL REVIEWS, 1988, 88 (08) :1453-1473
[6]   Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].
Dömling, A .
CHEMICAL REVIEWS, 2006, 106 (01) :17-89
[7]  
Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO
[8]  
2-U
[9]   Synthesis of vinyl spirolactones and lactams by sequential cross-coupling metathesis, [2+2] photocycloaddition and cyclobutane ring-opening [J].
Faure, S ;
Piva-Le Blanc, S ;
Piva, O .
TETRAHEDRON LETTERS, 1999, 40 (33) :6001-6004
[10]   Chemoenzymatic synthesis of enantiopure isopropyl (3R)- and (3S)-3-hydroxycyclohex-1-ene-1-carboxylates and their reduction to isomers of isopropyl 3-hydroxy-cyclohexane-1-carboxylate [J].
Fonteneau, L ;
Rosa, S ;
Buisson, D .
TETRAHEDRON-ASYMMETRY, 2002, 13 (06) :579-585