A sequential enantioselective, organocatalytic route to chiral 1,2-oxazines and chiral pyridazines

被引:35
作者
Kumarn, Sirirat [1 ]
Oelke, Alexander J. [1 ]
Shaw, David M. [1 ]
Longbottom, Deborah A. [1 ]
Ley, Steven V. [1 ]
机构
[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
关键词
D O I
10.1039/b708646f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A sequential, organocatalysed asymmetric reaction to access chiral 1,2- oxazines and chiral pyridazines is reported, which proceeds in moderate to good yields and good to excellent enantioselectivities.
引用
收藏
页码:2678 / 2689
页数:12
相关论文
共 100 条
[71]  
PUKKINEN J, 2004, ADV SYNTH CATAL, V346, P1077
[72]   Direct amino acid-catalyzed asymmetric desymmetrization of meso-compounds: Tandem aminoxylation/O-N bond heterolysis reactions [J].
Ramachary, DB ;
Barbas, CF .
ORGANIC LETTERS, 2005, 7 (08) :1577-1580
[73]   Asymmetric multicomponent reactions (AMCRs):: The new frontier [J].
Ramón, DJ ;
Yus, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (11) :1602-1634
[74]   Asymmetric construction of quaternary stereocenters by direct organocatalytic amination of α-substituted α-cyanoacetates and β-dicarbonyl compounds [J].
Saaby, S ;
Bella, M ;
Jorgensen, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (26) :8120-8121
[75]   REACTIONS OF PHOSPHORUS-COMPOUNDS .33. PREPARATION OF HETEROCYCLIC SPECIES FROM ALPHA-SUBSTITUTED VINYL PHOSPHONIUM SALTS - ANOMALOUS PRODUCTS FROM ISOPROPENYLPHOSPHONIUM HALIDES [J].
SCHWEIZE.EE ;
WEHMAN, AT ;
NYCZ, DM .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (08) :1583-1588
[76]   REACTIONS OF PHOSPHORUS-COMPOUNDS .41. THERMAL REARRANGEMENT OF HYDRAZONO VINYLPHOSPHONIUM SALTS TO PYRAZOLES [J].
SCHWEIZER, EE ;
HAYES, JE ;
HANAWALT, EM .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (14) :2591-2593
[77]   Asymmetric organocatalysis [J].
Seayad, J ;
List, B .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (05) :719-724
[78]   STUDIES IN PHOSPHINEMETHYLENE CHEMISTRY .14. REACTION OF VINYLIC PHOSPHONIUM BROMIDES WITH ORGANOLITHIUM REAGENTS [J].
SEYFERTH, D ;
FOGEL, J .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1966, 6 (03) :205-&
[79]   Utilisation of 1,3-dicarbonyl derivatives in multicomponent reactions [J].
Simon, C ;
Constantieux, T ;
Rodriguez, J .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (24) :4957-4980
[80]  
Streith J, 1996, SYNLETT, P189