Stereodirected Synthesis of Aryl α-C-Glycosides from 2-O-Arylsilyl-glucopyranosides

2003 ◽  
Vol 5 (20) ◽  
pp. 3763-3766 ◽  
Author(s):  
Cyril Rousseau ◽  
Olivier R. Martin
Keyword(s):  
Stereodirected Synthesis

Stereodirected synthesis of alkaloid-like quinolizidine systems

2018 ◽  
Vol 34 (2) ◽  
pp. 269-277
Author(s):  
Konstantin A. Krasnov ◽  
Alexandra A. Krasnova ◽  
Viktor G. Kartsev ◽  
Pavel V. Dorovatovskii ◽  
Yan V. Zubavichus ◽  
...  
Keyword(s):  
Stereodirected Synthesis

ChemInform Abstract: STEREODIRECTED SYNTHESIS OF ALL POSSIBLE ISOMERS OF 4-UREIDO-3-HYDROXY-2-(5′-ALKOXYCARBONYLBUTYL)THIOPHANE

1980 ◽  
Vol 11 (38) ◽  
Author(s):  
S. D. MIKHNO ◽  
T. M. FILIPPOVA ◽  
N. S. KULACHKINA ◽  
I. G. SUCHKOVA ◽  
V. M. BEREZOVSKII
Keyword(s):  
Stereodirected Synthesis

scholarly journals Book Review, Stereodirected Synthesis with Organoboranes

Synthesis ◽  
1996 ◽  
Vol 1996 (04) ◽  
pp. 551-552 ◽  
Author(s):  
K. Burgess
Keyword(s):  
Stereodirected Synthesis

ChemInform Abstract: Synthesis of Macrolide Antibiotics. Part 15. Stereodirected Synthesis of Erythronolide B by Coupling of the (C9-C13)+(C7-C8)+(C1-C6) Fragments.

ChemInform ◽  
1989 ◽  
Vol 20 (38) ◽  
Author(s):  
A. F. SVIRIDOV ◽  
M. S. ERMOLENKO ◽  
D. V. YASHUNSKII ◽  
B. S. BORODKIN ◽  
N. K. KOCHETKOV
Keyword(s):  
Macrolide Antibiotics ◽  
Erythronolide B ◽  
Stereodirected Synthesis

Diastereoisomeric 1-Benzyl-2,3-diphenylindanes: Stereodirected Synthesis and NMR Spectra

1998 ◽  
pp. 464-465
Author(s):  
José M. Aguirre ◽  
Elba N. Alesso ◽  
Graciela Y. Moltrasio Iglesias ◽  
Jorge D. Mufato
Keyword(s):  
Nmr Spectra ◽  
Stereodirected Synthesis

scholarly journals STEREODIRECTED SYNTHESIS OF (Е)- AND (Z)-ISOMERS OF 8-CHLOROOCT-7-EN-4-ONE

2017 ◽  
Vol 60 (1) ◽  
pp. 40
Author(s):  
Rinat N. Shakhmaev ◽  
Alisa Sh. Sunagatullina ◽  
Regina M. Alieva ◽  
Vladimir V. Zorin
Keyword(s):  
Phase Transfer Catalysis ◽  
Phase Transfer ◽  
Solid Phase ◽  
Reaction Selectivity ◽  
Standard Methods ◽  
Tetrabutylammonium Fluoride ◽  
Isomeric Purity ◽  
E And Z Isomers ◽  
Stereodirected Synthesis ◽  
High Stereoselectivity

For citation:Shakhmaev R.N., Sunagatullina A.Sh., Alieva R.M., Zorin V.V. Stereodirected synthesis of (Е)- and (Z)-isomers of 8-chlorooct-7-en-4-one. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2017. V. 60. N 1. P. 40-44. Reaction of ethyl 3-oxohexanoate with equimolar amounts of (E)- or (Z)-1,3-dichloro-propene under phase transfer catalysis conditions in the presence of K2CO3 afforded the corresponding monosubstituted (E)- or (Z)-isomers of ethyl 2-(3- chloroprop-2-en-1-yl)-3-oxohexa-noate and considerable amount of disubstituted derivatives (30-40%). In order to increase yields of monosubstituted derivatives we carried out research to test the known methods of selective monoalkylation of β-dicarbonyl compounds with respect to test substrates. Alkylation of ethyl 3-oxohexanoate in the presence of tetrabutylammonium fluoride and cobalt salts have not led to a significant increase in reaction selectivity, but in the reaction in solid in the absence of solvent the formation of disubstituted products is not practically observed. In the reaction of ethyl 3-oxo-hexanoate with (E)- or (Z)-isomers of 1,3-dichloropropene on the surface of Al2O3 impregnated with t-BuOK monosubstituted products are formed with the yields of 81 and 79%, respectively. Solid phase alkylation proceeds with high stereoselectivity, isomeric purity of target products are greater than 99%. Standard methods of monoalkylated ketoesters decarboxylation under acidic or basic conditions lead to low yields of the corresponding chlorovinyl ketones, best results are obtained at decarboxylation of (E)- or (Z)-isomers of ethyl 2-(3-chloroprop-2-en-1-yl)-3-oxohexa-noate in slightly modified Krapcho conditions. Carrying out the reaction in N-metrhylpirroli-dinone at a temperature of 130-140 °C in the presence of 3 eq. LiCl leads to (E)- and (Z)-isomers of 8-chlorooctyl-7-ene-4-one with 81 and 77% yields, respectively, and an isomeric purity of ~ 99%.

Sign in / Sign up

Export Citation Format

Share Document