BUSNCL3 MEDIATED Z-SELECTIVE 2-BUTENYLATION AND ERYTHRO-SELECTIVE 1-METHYL-2-PROPENYLATION OF ALDEHYDES BY 1-(TRIBUTYLSTANNYL)-2-BUTENE

被引：29

作者：

MIYAKE, H

YAMAMURA, K

机构：

来源：

CHEMISTRY LETTERS | 1992年 / 07期

关键词：

D O I：

10.1246/cl.1992.1369

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Butyltin trichloride mediated reaction of 1-(tributylstannyl)-2-butene with aldehydes is described. This reaction is useful as a stereoselective method for (Z)-2-butenylation and erythro-1-methy-2-propenylation of aldehydes.

引用

页码：1369 / 1372

页数：4

共 17 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
GAMBARO, A
PERUZZO, V
PLAZZOGNA, G
TAGLIAVINI, G
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 197 (01) : 45 - 50
[2] ALLYLSTANNATION .2. A TOTAL CIS-PREFERENCE IN THE ADDITION OF NORMAL-BU2CLSNCH(CH3)CH=CH2 TO ALDEHYDES
GAMBARO, A
GANIS, P
MARTON, D
PERUZZO, V
TAGLIAVINI, G
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1982, 231 (04) : 307 - 314
[3] AN ANOMALOUS CASE OF DIASTEREOFACIAL SELECTIVITY IN THE ADDITION OF CHIRAL ALLYLSTANNANES TO BENZALDEHYDE - IS THE INSIDE ALKOXY EFFECT INVOLVED
GUNG, BW
PEAT, AJ
SNOOK, BM
SMITH, DT
[J]. TETRAHEDRON LETTERS, 1991, 32 (04) : 453 - 456
[4] REMARKABLE INCREASE IN THE DIASTEREOFACIAL SELECTIVITY OF THE ADDITION OF BETA-METHYL ALPHA-(ALKOXY)ALLYLSTANNANE TO ALDEHYDES - SUBSTITUENT EFFECTS ON DIASTEREOFACIAL SELECTIVITY
GUNG, BW
SMITH, DT
WOLF, MA
[J]. TETRAHEDRON LETTERS, 1991, 32 (01) : 13 - 16
[5] IQUBAL J, 1989, TETRAHEDRON LETT, V30, P2421
[6] PALLADIUM-CATALYZED CARBONYL ALLYLATION BY ALLYLIC ALCOHOLS WITH SNCL2 - A SOLVATION-CONTROLLED DIASTEREOSELECTION
MASUYAMA, Y
TAKAHARA, JP
KURUSU, Y
[J]. TETRAHEDRON LETTERS, 1989, 30 (26) : 3437 - 3440
[7] SYNTHESIS OF HOMOALLYLIC ALCOHOLS FROM ALLYLIC PHOSPHATES AND ALDEHYDES WITH ORGANO-ALUMINUM REAGENT CONTAINING AL-SN LINKAGE
MATSUBARA, S
WAKAMATSU, K
MORIZAWA, Y
TSUBONIWA, N
OSHIMA, K
NOZAKI, H
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1985, 58 (04) : 1196 - 1199
[8] PD(O) CATALYZED HYDROSTANNATION OF CONJUGATED DIENES - A FACILE AND HIGHLY REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF (Z)-2-ALKENYLSTANNANES
MIYAKE, H
YAMAMURA, K
[J]. CHEMISTRY LETTERS, 1992, (03) : 507 - 508
[9] MIYAKE H, 1992, IN PRESS CHEM LETT
[10] CHEMOSPECIFIC CARBONYL ALLYLATION BY ALLYLTIN REAGENTS - SYNTHESIS OF GAMMA,DELTA-UNSATURATED ALCOHOLS
NARUTA, Y
USHIDA, S
MARUYAMA, K
[J]. CHEMISTRY LETTERS, 1979, (08) : 919 - 922

← 1 2 →