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

页码：7015 / 7018

页数：4

共 34 条

[1] CHIRAL PRECURSORS FOR THE SYNTHESIS OF ENANTIOMERICALLY PURE PIPERIDINES - TOTAL SYNTHESIS OF (R)-(-)-CONIINE
AMAT, M
LLOR, N
BOSCH, J
[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
ARSENIYADIS, S
HUANG, PQ
HUSSON, HP
[J]. TETRAHEDRON LETTERS, 1988, 29 (12) : 1391 - 1394
[3] ASYMMETRIC-SYNTHESIS .12. STEREOCONTROLLED ELECTROPHILIC-NUCLEOPHILIC ALPHA,ALPHA'-SUBSTITUTION OF THE PYRROLIDINE RING
ARSENIYADIS, S
HUANG, PQ
PIVETEAU, D
HUSSON, HP
[J]. TETRAHEDRON, 1988, 44 (09) : 2457 - 2470
[4] ALKALOIDAL VENOM MACE - OFFENSIVE USE BY A THIEF ANT
BLUM, MS
JONES, TH
HOLLDOBLER, B
FALES, HM
JAOUNI, T
[J]. NATURWISSENSCHAFTEN, 1980, 67 (03) : 144 - 145
[5] TERTIARY CARBINAMINES BY ADDITION OF ORGANOCERIUM REAGENTS TO NITRILES AND KETIMINES
CIGANEK, E
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (16) : 4521 - 4527
[6] ENANTIOPURE N-ACYLDIHYDROPYRIDONES AS SYNTHETIC INTERMEDIATES - AN ASYMMETRIC-SYNTHESIS OF SOLENOPSIN-A
COMINS, DL
BENJELLOUN, NR
[J]. TETRAHEDRON LETTERS, 1994, 35 (06) : 829 - 832
[7] ORGANOCERIUM ADDITIONS TO HYDRAZONES - EFFECTS OF REAGENT STOICHIOMETRY ON EFFICIENCY AND SELECTIVITY
DENMARK, SE
EDWARDS, JP
NICAISE, O
[J]. 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
GRANDJEAN, C
ROSSET, S
CELERIER, JP
LHOMMET, G
[J]. TETRAHEDRON LETTERS, 1993, 34 (28) : 4517 - 4518
[10] ULTRASOUND ASSISTED PREPARATION OF ORGANOCERIUM REAGENTS
GREEVES, N
LYFORD, L
[J]. TETRAHEDRON LETTERS, 1992, 33 (33) : 4759 - 4760

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