Imine allylation by allylic trimethylsilanes via in situ formation of N-tosyliminium species from carbonyl compounds and toluene-p-sulfonamide with SnCl2 and N-chlorosuccinimide:: regioselection and diastereoselection

被引:29
作者
Masuyama, Y [1 ]
Tosa, J [1 ]
Kurusu, Y [1 ]
机构
[1] Sophia Univ, Dept Chem, Chiyoda Ku, Tokyo 1028554, Japan
关键词
D O I
10.1039/a902789k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
N-Tosyliminium species, prepared in situ from carbonyl compounds and TsNH2 with SnCl2 and N-chlorosuccinimide, undergo nucleophilic addition of allylic silanes (imine allylation) to produce the corresponding homoallylic amines; the imine allylation by but-2-enyltrimethylsilane with aldehydes and TsNH2 leads to regio- and diastereoselection to produce anti 1-substituted 2-methylbut-3-enylamines.
引用
收藏
页码:1075 / 1076
页数:2
相关论文
共 17 条
[1]   ENANTIOSELECTIVE SYNTHESIS OF HOMOALLYLIC AMINES BY ADDITION OF ALLYLMETAL REAGENTS TO IMINES DERIVED FROM (S)-VALINE ESTERS [J].
BASILE, T ;
BOCOUM, A ;
SAVOIA, D ;
UMANIRONCHI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) :7766-7773
[2]   CATALYTIC ALLYLATION OF IMINES PROMOTED BY LANTHANIDE TRIFLATES [J].
BELLUCCI, C ;
COZZI, PG ;
UMANIRONCHI, A .
TETRAHEDRON LETTERS, 1995, 36 (40) :7289-7292
[3]   Organometallic reactions in aqueous media. Indium-mediated allylation of sulfonimines [J].
Chan, TH ;
Lu, WS .
TETRAHEDRON LETTERS, 1998, 39 (47) :8605-8608
[4]   CONDENSATION REACTION OF TRICHLOROSILANE WITH ALLYLIC CHLORIDES CATALYZED BY COPPER SALTS IN PRESENCE OF A TERTIARY AMINE [J].
FURUYA, N ;
SUKAWA, T .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 96 (01) :C1-C3
[5]   REACTIONS OF ALLYLSTANNANES WITH INSITU GENERATED IMMONIUM SALTS IN PROTIC SOLVENT - A FACILE AMINOMETHANO DESTANNYLATION PROCESS [J].
GRIECO, PA ;
BAHSAS, A .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (07) :1378-1380
[6]   GENERATION OF N-ACYL IMINIUM IONS FROM IONIZATION-REARRANGEMENT REACTIONS OF N-TRIFLYLOXY AMIDES [J].
HOFFMAN, RV ;
NAYYAR, NK ;
SHANKWEILER, JM ;
KLINEKOLE, BW .
TETRAHEDRON LETTERS, 1994, 35 (20) :3231-3234
[7]  
HOFFMANN RW, 1987, LIEBIGS ANN CHEM, P215
[8]   REACTION OF N-ACYL-ALPHA-METHOXYAMINES WITH ORGANOZINC REAGENTS - CONVENIENT METHOD FOR THE SYNTHESIS OF HOMOALLYLAMINES AND BETA-AMINO ESTERS [J].
KISE, N ;
YAMAZAKI, H ;
MABUCHI, T ;
SHONO, T .
TETRAHEDRON LETTERS, 1994, 35 (10) :1561-1564
[9]  
Kobayashi S, 1997, SYNLETT, P1099
[10]   REACTIONS OF ALLYLSILANES WITH SIMPLE IMINIUM SALTS IN WATER - A FACILE ROUTE TO PIPERIDINES VIA AN AMINOMETHANO DESILYLATION CYCLIZATION PROCESS [J].
LARSEN, SD ;
GRIECO, PA ;
FOBARE, WF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (12) :3512-3513