STEREOSELECTIVE SYNTHESIS OF BOTH DIASTEREOMERS OF THE ALPHA-METHYL-BETA-HYDROXY-BETA-ALKYL(ARYL) UNITS BY USE OF TIN(II) TRIFLATE-MEDIATED ALDOL REACTION

被引：20

作者：

KOBAYASHI, S

HACHIYA, I

机构：

[1] Department of Applied Chemistry, Faculty of Science, Science University of Tokyo (SUT), Tokyo 162, Kagurazaka, Shinjuku-ku

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 05期

关键词：

D O I：

10.1021/jo00031a004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Both diastereomers of the alpha-methyl-beta-hydroxy-beta-alkyl(aryl) units are prepared by the tin(II) triflate-mediated aldol reaction of 1-(ethylthio)-1-(trimethylsiloxy)propene with alpha-keto esters in high selectivities.

引用

页码：1324 / 1326

页数：3

共 23 条

[1] Chan T. H., 1979, TETRAHEDRON LETT, V20, P4029
[2] DIASTEREOSELECTIVE ALDOL REACTIONS USING BETA-KETO IMIDE DERIVED ENOLATES - A VERSATILE APPROACH TO THE ASSEMBLAGE OF POLYPROPIONATE SYSTEMS
EVANS, DA
CLARK, JS
METTERNICH, R
NOVACK, VJ
SHEPPARD, GS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) : 866 - 868
[3] LEWIS ACID MEDIATED ALDOL CONDENSATIONS USING THIOESTER SILYL KETENE ACETALS
GENNARI, C
BERETTA, MG
BERNARDI, A
MORO, G
SCOLASTICO, C
TODESCHINI, R
[J]. TETRAHEDRON, 1986, 42 (03) : 893 - 909
[4] ORGANOLANTHANIDE CATALYSIS OF A MUKAIYAMA ADDITION-REACTION
GONG, L
STREITWIESER, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (26) : 6235 - 6236
[5] ACYCLIC STEREOSELECTION .36. SIMPLE DIASTEREOSELECTION IN THE LEWIS ACID MEDIATED REACTIONS OF ENOL SILANES WITH ALDEHYDES
HEATHCOCK, CH
DAVIDSEN, SK
HUG, KT
FLIPPIN, LA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (15) : 3027 - 3037
[6] HEATHCOCK CH, 1984, ASYMMETRIC SYNTHESIS, V3, pCH2
[7] CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL-PRODUCTS .32. SYNTHESIS OF ERYTHRONOLIDE A VIA A VERY EFFICIENT MACROLACTONIZATION UNDER USUAL ACYLATION CONDITIONS WITH THE YAMAGUCHI REAGENT
HIKOTA, M
SAKURAI, Y
HORITA, K
YONEMITSU, O
[J]. TETRAHEDRON LETTERS, 1990, 31 (44) : 6367 - 6370
[8] ASYMMETRIC ALDOL REACTION BETWEEN ACHIRAL SILYL ENOL ETHERS AND ACHIRAL ALDEHYDES BY USE OF A CHIRAL PROMOTER SYSTEM
KOBAYASHI, S
UCHIRO, H
FUJISHITA, Y
SHIINA, I
MUKAIYAMA, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) : 4247 - 4252
[9] THE EFFICIENT CATALYTIC ASYMMETRIC ALDOL-TYPE REACTION
KOBAYASHI, S
FUJISHITA, Y
MUKAIYAMA, T
[J]. CHEMISTRY LETTERS, 1990, (08) : 1455 - 1458
[10] A HIGHLY ENANTIOSELECTIVE SYNTHESIS OF 2-SUBSTITUTED MALATES BY ASYMMETRIC ALDOL REACTION
KOBAYASHI, S
FUJISHITA, Y
MUKAIYAMA, T
[J]. CHEMISTRY LETTERS, 1989, (11) : 2069 - 2072

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