Allylation of imines with allyltrimethylsilane and experimental evidences for a fluoride-triggered autocatalysis mechanism of the Sakurai-Hosomi reaction

被引:78
作者
Wang, DK [1 ]
Zhou, YG [1 ]
Tang, Y [1 ]
Hou, XL [1 ]
Dai, LX [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Organomet Chem Lab, Shanghai 200032, Peoples R China
关键词
D O I
10.1021/jo980767y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This article reports the reaction of allyltrimethylsilane 1 with aldimines 2 in the presence of tetra-n-butylammonium fluoride to give the corresponding homoallylamines 3 in moderate to excellent yields. The allylation mechanism of imines as well as that of aldehydes can be reasonably interpreted by a fluoride-triggered autocatalytic procedure.
引用
收藏
页码:4233 / 4237
页数:5
相关论文
共 50 条
[1]  
ABLE EW, 1975, J ORGANOMET CHEM, V84, P199
[2]   METALLIC BISMUTH AND TANTALUM MEDIATED C-ALLYLATION OF ALDIMINES WITH ALLYL BROMIDE [J].
BHUYAN, PJ ;
PRAJAPATI, D ;
SANDHU, JS .
TETRAHEDRON LETTERS, 1993, 34 (49) :7975-7976
[3]   New computational and experimental evidence for the mechanism of the Sakurai reaction [J].
Bottoni, A ;
Costa, AL ;
Di Tommaso, D ;
Rossi, I ;
Tagliavini, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12131-12135
[4]   ADDITION OF SILYLATED HYDROCARBONS HAVING ACTIVATED SI-C BOND TO ALPHA CHLORAL CARBONYL-COMPOUNDS [J].
CALAS, R ;
DUNOGUES, J ;
DELERIS, G ;
PISCIOTT.F .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 69 (02) :C15-C17
[5]  
CAMPBELL KN, 1944, J AM CHEM SOC, V66, P822
[6]   LIQUID CRYSTALS .2. EFFECTS OF TERMINAL GROUP SUBSTITUTION ON MESOMORPHIC BEHAVIOR OF SOME BENZYLIDENEANILINES [J].
CASTELLANO, JA ;
GOLDMACHER, JE ;
BARTON, LA ;
KANE, JS .
JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (09) :3501-+
[7]   A CONCISE CHEMICAL SYNTHESIS OF (+)-3-DEOXY-D-GLYCERO-D-GALACTO-NONULOSONIC ACID (KDN) [J].
CHAN, TH ;
LI, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (10) :747-748
[8]  
Chen DL, 1996, TETRAHEDRON LETT, V37, P295
[9]   REACTIVITY OF PENTACOORDINATE AND HEXACOORDINATE SILICON-COMPOUNDS AND THEIR ROLE AS REACTION INTERMEDIATES [J].
CHUIT, C ;
CORRIU, RJP ;
REYE, C ;
YOUNG, JC .
CHEMICAL REVIEWS, 1993, 93 (04) :1371-1448
[10]   ENANTIOSELECTIVE SYNTHESIS OF THE C(18)-C(35) SEGMENT OF IMMUNOSUPPRESSANT FK-506 USING EFFICIENT NEW METHODOLOGY [J].
COREY, EJ ;
HUANG, HC .
TETRAHEDRON LETTERS, 1989, 30 (39) :5235-5238