ISSN:
1434-193X
Keywords:
Sonogashira-Linstrumelle cross-coupling
;
Stille cross-coupling
;
Protected enynals
;
Transacetalisation
;
Pent-2-en-4-yn-1-al
;
Deca-2,8-diene-4,6-diyne-1,10-dial
;
Dienediynes
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
(3E)-5,5-Diethoxypent-3-en-1-yne was stereospecifically prepared by Sonogashira-Linstrumelle cross-coupling between (E)-3-iodoacrolein diethylacetal and (trimethylsilyl)acetylene. The (Z) isomer was obtained by Stille cross-coupling between the corresponding (Z)-vinyltin and 1-bromo-2-(trimethylsilyl)acetylene. In the case of the (E) isomer, transacetalisation occurred without isomerization affording a large variety of (E)-enynals protected as acetals. It has also been shown to be possible to obtain the corresponding (E,E)-dienediyne through sp-sp homocoupling under appropriate experimental conditions.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
Permalink
