Intramolecular alkene–alkyne metathesis and 1,4-cis-hydrogenation as a stereocontrolled route to compounds with exocyclic double bonds

Intramolecular alkene–alkyne metathesis and 1,4-cis-hydrogenation as a stereocontrolled route to compounds with exocyclic double bonds

Intramolecular alkene-alkyne metathesis of diethyl (but-3-en-1-yl)(propargyl)malonate affords diethyl 3-vinylcyclohex-3-ene-1,1-dicarboxylate whose conjugated diene system was 1,4- cis -hydrogenated in the presence of η 6 -(naphthalene)chromium tricarbonyl. The exocyclic double bond of thus formed d...

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Veröffentlicht in:Russian chemical bulletin 2020, Vol.69 (1), p.169-171
Hauptverfasser: Vasil’ev, A. A., Engman, L., Serebryakov, E. P.
Format: Artikel
Sprache:eng
Schlagworte:
4-cis-hydrogenation
Alkynes
Brief Communication
Chemical bonds
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
dienes
enynes
Inorganic Chemistry
Metathesis
Naphthalene
Organic Chemistry
stereocontrolled synthesis
Tricarbonylchromium
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Zusammenfassung:Intramolecular alkene-alkyne metathesis of diethyl (but-3-en-1-yl)(propargyl)malonate affords diethyl 3-vinylcyclohex-3-ene-1,1-dicarboxylate whose conjugated diene system was 1,4- cis -hydrogenated in the presence of η 6 -(naphthalene)chromium tricarbonyl. The exocyclic double bond of thus formed diethyl 3-ethylidenecyclohexane-1,1-dicarboxylate is strictly ( E )-configured.
ISSN:1066-5285
1573-9171
1573-9171
DOI:10.1007/s11172-020-2739-1