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Stereoselective Synthesis of ( E )‐ and ( Z )‐Acetals of Pent‐2‐en‐4‐yn‐1‐al and Related Dienynes and Dienediynes
Author(s) -
Suzenet Franck,
Parrain JeanLuc,
Quintard JeanPaul
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199911)1999:11<2957::aid-ejoc2957>3.0.co;2-7
Subject(s) - chemistry , stille reaction , isomerization , sonogashira coupling , stereoselectivity , acetylene , trimethylsilyl , stereochemistry , medicinal chemistry , organic chemistry , palladium , catalysis
(3 E )‐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.