ALPHA-REGIOSELECTIVE CARBONYL ALLYLATION BY AN ALLYLIC TIN COMPOUND PREPARED FROM 1-BROMOBUT-2-ENE AND TIN(II) BROMIDE AT A NONPOLAR ORGANIC-AQUEOUS INTERFACE

被引:15
作者
MASUYAMA, Y
KISHIDA, M
KURUSU, Y
机构
关键词
D O I
10.1039/c39950001405
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
1-Bromobut-2-ene on a dichloromethane-water biphasic system at 25 degrees C causes alpha-regioselective addition to aldehydes with SnBr2 to produce 1-substituted pent-3-en-1-ols, and causes gamma-regioselective addition to aldehydes with SnBr2-Bu(4)NBr to produce 1-substituted 2-methylbut-3-en-1-ols.
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页码:1405 / 1406
页数:2
相关论文
共 10 条
[1]   ALLYLBUTYLTIN HALIDES (CH2=CHCH2)SNBU3-NCLN(N=0,1,2,3) - PREPARATION, C-13 NMR CHARACTERIZATION AND ALLYLSTANNYLATION ABILITY TOWARDS KETONES AND ALDEHYDES [J].
GAMBARO, A ;
PERUZZO, V ;
PLAZZOGNA, G ;
TAGLIAVINI, G .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 197 (01) :45-50
[2]   CARBONYL ALLYLATION BY VINYL EPOXIDES WITH SNCL2-TBA OR SNCL2-LII - APPLICATION TO THE DIASTEREOSELECTIVE SYNTHESIS OF 1,3-DIOLS [J].
MASUYAMA, Y ;
NAKATA, J ;
KURUSU, Y .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (10) :2598-2599
[3]   ULTRASOUND-PROMOTED PALLADIUM-CATALYZED CARBONYL ALLYLATION BY ALLYLIC ALCOHOLS WITH TIN(II) CHLORIDE IN NONPOLAR-SOLVENTS [J].
MASUYAMA, Y ;
HAYAKAWA, A ;
KISHIDA, M ;
KURUSU, Y .
INORGANICA CHIMICA ACTA, 1994, 220 (1-2) :155-159
[5]  
Masuyama Y., 1994, ADV MET ORG, V3, P255
[6]   AN EFFICIENT METHOD FOR THE PREPARATION OF HOMOALLYLIC ALCOHOL DERIVATIVES BY THE REACTION OF ALLYL IODIDE WITH CARBONYL-COMPOUNDS IN THE PRESENCE OF STANNOUS HALIDE [J].
MUKAIYAMA, T ;
HARADA, T ;
SHODA, SI .
CHEMISTRY LETTERS, 1980, (12) :1507-1510
[7]   ALLYLATION OF ALDEHYDES AND KETONES IN THE PRESENCE OF WATER BY ALLYLIC BROMIDES, METALLIC TIN, AND ALUMINUM [J].
NOKAMI, J ;
OTERA, J ;
SUDO, T ;
OKAWARA, R .
ORGANOMETALLICS, 1983, 2 (01) :191-193
[8]   REGIOREVERSED ADDITION OF CROTYLMAGNESIUM CHLORIDE TO CARBONYL-COMPOUNDS IN THE PRESENCE OF ALCL3 [J].
YAMAMOTO, Y ;
MARUYAMA, K .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (09) :1564-1565
[9]   SELECTIVE REACTIONS USING ALLYLIC METALS [J].
YAMAMOTO, Y ;
ASAO, N .
CHEMICAL REVIEWS, 1993, 93 (06) :2207-2293
[10]   ALLYLBARIUM REAGENTS - UNPRECEDENTED REGIOSELECTIVE AND STEREOSELECTIVE ALLYLATION REACTIONS OF CARBONYL-COMPOUNDS [J].
YANAGISAWA, A ;
HABAUE, S ;
YASUE, K ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (14) :6130-6141