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 eta(6)-(naphthalene)chromium tricarbonyl. The exocyclic double bond of thus formed diethyl 3-ethylidenecyclohexane-1,1-dicarboxylate is strictly (E)-configured.

Subject headings

NATURVETENSKAP  -- Kemi -- Organisk kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences -- Organic Chemistry (hsv//eng)

Keyword

enynes

dienes

metathesis

1

4-cis-hydrogenation

stereocontrolled synthesis

Publication and Content Type

ref (subject category)

art (subject category)