5-MEMBERED RING FORMATION OF 2-HYDROXYALKYL MALONATE AND ACETOACETATE DERIVATIVES - THE PROBLEM OF O-ALKYLATION VERSUS C-ALKYLATION

被引：10

作者：

ADAMS, E ^{[1
]}

HIEGEMANN, M ^{[1
]}

DUDDECK, H ^{[1
]}

WELZEL, P ^{[1
]}

机构：

[1] RUHR UNIV BOCHUM,FAK CHEM,POSTFACH 102148,W-4630 BOCHUM,GERMANY

来源：

TETRAHEDRON | 1990年 / 46卷 / 17期

关键词：

D O I：

10.1016/S0040-4020(01)87922-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cyclization reactions of type 32, 34, 36, 37/38 compounds have been studied with the aim of achieving a carbon-carbon bond forming reaction at C-2 of optically active glycerol derivatives as indicated in Scheme 1. In all cases O-alkylation at the proximal CO group has been observed. © 1990.

引用

页码：5975 / 5992

页数：18

共 61 条

[1] CYCLIZATIONS OF ACETOACETATES TO ALPHA-ACYLTETRONIC ACIDS
AGER, DJ
MOLE, SJ
[J]. TETRAHEDRON LETTERS, 1988, 29 (38) : 4807 - 4810
[2] CONSIDERED AS REAGENTS AND SYNTHETIC METHODS .46. 1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE(DBU) - AN EFFECTIVE BASE FOR THE INTRODUCTION OF TERT-BUTYLDIMETHYLSILYL GROUP IN ORGANIC-COMPOUNDS
AIZPURUA, JM
PALOMO, C
[J]. TETRAHEDRON LETTERS, 1985, 26 (04) : 475 - 476
[3] ARNETT EM, 1987, GAZZ CHIM ITAL, V117, P237
[4] ION-PAIRING AND REACTIVITY OF ENOLATE ANIONS .6. KINETICS AND THERMODYNAMICS FOR REACTION OF ALKALI ACETYLACETONATES WITH ALKYL-HALIDES IN DIMETHYL-SULFOXIDE
ARNETT, EM
MAROLDO, SG
SCHRIVER, GW
SCHILLING, SL
TROUGHTON, EB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (07) : 2091 - 2099
[5] RULES FOR RING-CLOSURE - APPLICATION TO INTRAMOLECULAR ALDOL CONDENSATIONS IN POLYKETONIC SUBSTRATES
BALDWIN, JE
LUSCH, MJ
[J]. TETRAHEDRON, 1982, 38 (19) : 2939 - 2947
[6] ALKYLATION OF ETHYL 4,4,4-TRIFLUOROACETOACETATE - 1ST EXAMPLE OF A REVERSIBLE O-ALKYLATION PROCESS LEADING TO C-ALKYLATION
BEGUE, JP
CHARPENTIERMORIZE, M
NEE, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (02) : 83 - 84
[7] BERLAGE U, 1987, TETRAHEDRON LETT, V27, P3091
[8] BOSSERT F, 1979, ARZNEIMITTEL-FORSCH, V29-1, P226
[9] SURFACE ENHANCED ENANTIODIFFERENTIATION IN REACTIONS OF CHIRAL ACETOACETATES
BRAM, G
CABARET, D
WELVART, Z
GERAGHTY, NWA
GARVEY, J
[J]. TETRAHEDRON LETTERS, 1988, 29 (36) : 4615 - 4618
[10] ION-PAIRING AND REACTIVITY OF THE ALKALI-METAL AND ALKALINE-EARTH-METAL DERIVATIVES OF ETHYL (5-BROMOPENTYL)ACETOACETATE
CACCIAPAGLIA, R
MANDOLINI, L
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (11) : 2579 - 2582

← 1 2 3 4 5 6 7 →