DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESES OF (-)-CONIINE, (-)-SOLENOPSIN-A, (-)-SOLENOPSIS-FUGAX VENOM AND (-)-XENOVENINE VIA DEOXYGENATIVE DECARBOXYLATION OF 2-CARBONYLSULTAM-SUBSTITUTED N-HYDROXY-PIPERIDINES AND N-HYDROXY-PYRROLIDINES

被引：79
作者：
OPPOLZER, W
BOCHET, CG
MERIFIELD, E
机构：
[1] Départment de Chimie Organique, Université de Genève
来源：
TETRAHEDRON LETTERS | 1994年 / 35卷 / 38期
关键词：
D O I：
10.1016/0040-4039(94)88213-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Heating cyclic 2-carbonylsultam-substituted N-hydroxylamines 4 with NaH yields sultam auxiliary 8 and imines 10, which are trapped in situ either by i-Bu(2)AlH or organocerium reagents to give 2 enantiomerically pure 2-mono- or trans-2,6(2,5)-disubstituted piperidines (pyrrolidines) 11 or 12.
引用
收藏
页码：7015 / 7018
页数：4
相关论文
共 34 条
[1]   CHIRAL PRECURSORS FOR THE SYNTHESIS OF ENANTIOMERICALLY PURE PIPERIDINES - TOTAL SYNTHESIS OF (R)-(-)-CONIINE [J].
AMAT, M ;
LLOR, N ;
BOSCH, J .
TETRAHEDRON LETTERS, 1994, 35 (14) :2223-2226
[2]   ASYMMETRIC-SYNTHESIS .14. A SHORT AND EFFICIENT SYNTHESIS OF 3,5-DISUBSTITUTED PYRROLIZIDINE ALKALOIDS VIA THE CN(R,S) METHOD [J].
ARSENIYADIS, S ;
HUANG, PQ ;
HUSSON, HP .
TETRAHEDRON LETTERS, 1988, 29 (12) :1391-1394
[3]   ASYMMETRIC-SYNTHESIS .12. STEREOCONTROLLED ELECTROPHILIC-NUCLEOPHILIC ALPHA,ALPHA'-SUBSTITUTION OF THE PYRROLIDINE RING [J].
ARSENIYADIS, S ;
HUANG, PQ ;
PIVETEAU, D ;
HUSSON, HP .
TETRAHEDRON, 1988, 44 (09) :2457-2470
[4]   ALKALOIDAL VENOM MACE - OFFENSIVE USE BY A THIEF ANT [J].
BLUM, MS ;
JONES, TH ;
HOLLDOBLER, B ;
FALES, HM ;
JAOUNI, T .
NATURWISSENSCHAFTEN, 1980, 67 (03) :144-145
[5]   TERTIARY CARBINAMINES BY ADDITION OF ORGANOCERIUM REAGENTS TO NITRILES AND KETIMINES [J].
CIGANEK, E .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (16) :4521-4527
[6]   ENANTIOPURE N-ACYLDIHYDROPYRIDONES AS SYNTHETIC INTERMEDIATES - AN ASYMMETRIC-SYNTHESIS OF SOLENOPSIN-A [J].
COMINS, DL ;
BENJELLOUN, NR .
TETRAHEDRON LETTERS, 1994, 35 (06) :829-832
[7]   ORGANOCERIUM ADDITIONS TO HYDRAZONES - EFFECTS OF REAGENT STOICHIOMETRY ON EFFICIENCY AND SELECTIVITY [J].
DENMARK, SE ;
EDWARDS, JP ;
NICAISE, O .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (03) :569-578
[8]  
ENDERS D, 1993, LIEBIGS ANN CHEM, P173
[9]   A NEW SYNTHESIS OF ANT VENOM ALKALOID - (3S,5R,8S)-3-HEPTYL-5-METHYLPYRROLIZIDINE [J].
GRANDJEAN, C ;
ROSSET, S ;
CELERIER, JP ;
LHOMMET, G .
TETRAHEDRON LETTERS, 1993, 34 (28) :4517-4518
[10]   ULTRASOUND ASSISTED PREPARATION OF ORGANOCERIUM REAGENTS [J].
GREEVES, N ;
LYFORD, L .
TETRAHEDRON LETTERS, 1992, 33 (33) :4759-4760
1234