An Unexpended Stereocontrolled Rearrangement of Ethyl 4-Hydroxy-4-(substituted phenyl)-2-butynoate to Tetrasubstituted Alkenes with MeSOCl2
CHEMISTRYSELECT, cilt.7, sa.33, 2022 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 7 Sayı: 33
- Basım Tarihi: 2022
- Doi Numarası: 10.1002/slct.202201499
- Dergi Adı: CHEMISTRYSELECT
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier
- Anahtar Kelimeler: Alkynes, Hydrochlorination, Mesylation, Stereocontrolled rearrangement, Tetrasubstituted alkene, STEREOSELECTIVE-SYNTHESIS, COUPLING REACTIONS, ALKYNES, PALLADIUM, HYDROCHLORINATION, CHLORIDES, TRI
- Atatürk Üniversitesi Adresli: Evet
Özet
Tetrasubstituted alkene derivatives are synthetically important compounds and one of the important research areas in organic chemistry. Stereoselective synthesis of all-carbon tetrasubstituted alkenes is a challenging problem in chemical synthesis because of the uncontrolled Z/E stereoselectivity. Here we described an unexpended stereocontrolled rearrangement for the synthesis of tetrasubstituted alkenes, each group different from the other. The reaction of ethyl 4-hydroxy-4-(substituted phenyl)-2-butynoate derivatives with methanesulfonyl chloride and triethylamine gave in an interesting manner syn-selective tetrasubstituted alkene, containing the sulfonate ester and the chlorine atom. The Z-configuration of the chlorovinyl sulfonate esters was determined by X-ray crystal analysis. The parameters (such as amount of equivalent, solvent, and temperature) that will affect product formation were examined and the optimum conditions for formation were determined.