REVERSAL OF STEREOSELECTIVITY IN THE EVANS ALDOL REACTION OF ALPHA,ALPHA-DIFLUORO AND ALPHA,ALPHA,ALPHA-TRIFLUORO CARBONYL-COMPOUNDS

被引：26

作者：

ISEKI, K ^{[1
]}

OISHI, S ^{[1
]}

TAGUCHI, T ^{[1
]}

KOBAYASHI, Y ^{[1
]}

机构：

[1] TOKYO COLL PHARM,HACHIOJI,TOKYO 19203,JAPAN

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 50期

关键词：

D O I：

10.1016/S0040-4039(00)61475-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Evans aldol reaction of hexafluoroacetone and trifluoroacetaldehyde causes reversal of stereoselectivity?v. The boron enolate derived from oxazolidinone 1 reacts with trifluoroacetaldehyde to give anti and ''non-Evans'' syn aldols with stereoselectivities in the range, 7:3-17:3.

引用

页码：8147 / 8150

页数：4

共 13 条

[1] AKITA H, 1986, CHEM PHARM BULL, V34, P2656
[2] PREPARATION AND PROPERTIES OF CHIRAL FLUOROORGANIC COMPOUNDS
BRAVO, P
RESNATI, G
[J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (10) : 661 - 692
[3] KINETIC RESOLUTIONS IN ANTIALDOL REACTIONS WITH RACEMIC 2-PHENYLTHIO ALDEHYDES - ASYMMETRIC-SYNTHESIS OF CYCLIC ETHERS AND LACTONES WITH PHENYLTHIO MIGRATION
CHIBALE, K
WARREN, S
[J]. TETRAHEDRON LETTERS, 1992, 33 (30) : 4369 - 4372
[4] ACYCLIC STEREOSELECTION .48. REVERSAL OF STEREOCHEMISTRY IN THE ALDOL REACTIONS OF A CHIRAL BORON ENOLATE
DANDA, H
HANSEN, MM
HEATHCOCK, CH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) : 173 - 181
[5] GAGE JR, 1990, ORG SYNTH, V68, P83
[6] ON THE REVERSAL OF THE STEREOSELECTIVITY IN THE EVANS ALDOL REACTION OF ALPHA-AMINO ALDEHYDES
HAYASHI, K
HAMADA, Y
SHIOIRI, T
[J]. TETRAHEDRON LETTERS, 1991, 32 (49) : 7287 - 7290
[7] Heathcock C., 1990, ALDRICHIM ACTA, V23, P99
[8] DIASTEREOSELECTIVE TRIFLUOROMETHYLATION OF CHIRAL IMIDE ENOLATES WITH IODOTRIFLUOROMETHANE MEDIATED BY TRIETHYLBORANE
ISEKI, K
NAGAI, T
KOBAYASHI, Y
[J]. TETRAHEDRON LETTERS, 1993, 34 (13) : 2169 - 2170
[9] PHEROMONE SYNTHESIS .35. STEREOSELECTIVE SYNTHESIS OF OPTICALLY-ACTIVE FORMS OF DELTA-MULTISTRIATIN, THE ATTRACTANT FOR EUROPEAN POPULATIONS OF THE SMALLER EUROPEAN ELM BARK BEETLE
MORI, K
IWASAWA, H
[J]. TETRAHEDRON, 1980, 36 (01) : 87 - 90
[10] PREPARATION BY YEAST REDUCTION AND DETERMINATION OF THE SENSE OF CHIRALITY OF ENANTIOMERICALLY PURE ETHYL (-)-4,4,4-TRICHLORO-3-HYDROXYBUTANOATE AND (+)-4,4,4-TRIFLUORO-3-HYDROXYBUTANOATE
SEEBACH, D
RENAUD, P
SCHWEIZER, WB
ZUGER, MF
BRIENNE, MJ
[J]. HELVETICA CHIMICA ACTA, 1984, 67 (07) : 1843 - 1853

← 1 2 →