Synthesis of α-substituted allylic amines via a modified bruylants reaction

被引:29
作者
Agami, C [1 ]
Couty, F [1 ]
Evano, G [1 ]
机构
[1] Univ Paris 06, CNRS, Lab Synthese Asymetr, F-75005 Paris, France
关键词
D O I
10.1021/ol0059908
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
GRAPHICS Silver tetrafluoroborate, used as an iminium ion promoter from a amino nitriles, is an efficient additive in the Bruylants reaction involving vinylic Grignards. Improved yields of allylic amines were obtained when the starting a-amino nitrile was treated with this silver salt prior to its reaction with the vinylic Grignard. This improvement was not observed in the case of acetylenic Grignards, The reactivity of other vinyl organometallics (M = Zn, Li, Al, Cu, Si) was briefly examined.
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收藏
页码:2085 / 2088
页数:4
相关论文
共 14 条
[1]   ON THE RELATIVE REACTIVITY OF CARBONYL AND IMINIUM ION MOIETIES [J].
AGAMI, C ;
COUTY, F ;
HAMON, L ;
PUCHOT, C .
TETRAHEDRON LETTERS, 1992, 33 (25) :3645-3646
[2]  
AHBLRECHT H, 1985, SYNTHESIS-STUTTGART, P743
[3]  
AHLBRECHT H, 1998, CHEM REV, V98, P1689
[4]  
Bruylants P., 1924, B SOC CHIM BELG, V33, P467
[5]   trans-cis-Isomerization of trans-2-allyl-6-alkyl(aryl)-1,2,3,6-tetrahydropyridines on heating with triallylborane. Synthesis of (+/-)-dihydropinidine. [J].
Bubnov, YN ;
Klimkina, EV ;
Ignatenko, AV ;
Gridnev, ID .
TETRAHEDRON LETTERS, 1997, 38 (26) :4631-4634
[6]   Asymmetric synthesis of dienomycin C [J].
Comins, DL ;
Green, GM .
TETRAHEDRON LETTERS, 1999, 40 (02) :217-218
[7]   REGIOSELECTIVE OXIDATION OF PIPERIDINE-3 DERIVATIVES - A SYNTHETIC ROUTE TO 2,5-SUBSTITUTED PIPERIDINES [J].
COMPERNOLLE, F ;
SALEH, MA ;
VANDENBRANDEN, S ;
TOPPET, S ;
HOORNAERT, G .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2386-2390
[8]   IMINIUM ION AND ACYLIMINIUM ION INITIATED CYCLIZATION REACTIONS OF VINYLSILANES - REGIOCONTROLLED SYNTHESIS OF TETRAHYDROPYRIDINES AND RELATED HETEROCYCLES [J].
FLANN, C ;
MALONE, TC ;
OVERMAN, LE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (20) :6097-6107
[9]   CHIRAL 1,4-DIHYDROPYRIDINE EQUIVALENTS - A NEW APPROACH TO THE ASYMMETRIC-SYNTHESIS OF ALKALOIDS - THE ENANTIOSPECIFIC SYNTHESIS OF (+)-CONIINE AND (-)-CONIINE AND DIHYDROPINIDINE [J].
GUERRIER, L ;
ROYER, J ;
GRIERSON, DS ;
HUSSON, HP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (26) :7754-7755
[10]  
Ha J.D., 1999, J AM CHEM SOC, V121, P10012, DOI DOI 10.1021/ja9925958