Carbon-carbon bond formation in regio- and stereoselective palladium-catalyzed cyclization of allene-substituted conjugated dienes

• Regio- and stereoselective palladium-catalyzed reactions of allene-substituted 1,3-dienes 1 in acetic acid at room temperature lead to cyclization with formation of a carbon-carbon bond between the middle carbon of the allene and the terminal carbon of the 1,3-diene. Two different types of reactions, both that constitute 1,4-carboacetoxylations of the 1,3-diene, have been developed. In one of the reactions, Pd(II) catalyzes the oxidation of 1 to bicyclic compounds 2, and in the other, Pd(0) catalyzes the transformation of 1 to bicyclic compounds 3. The products 2 are useful for further synthetic transformations and undergo Diels-Alder reactions with dienophiles to give polycyclic ring systems.

Ämnesord

NATURVETENSKAP  -- Kemi (hsv//swe)

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

Nyckelord

(ETA-1

ETA-3-OCTADIENEDIYL)PALLADIUM COMPLEXES

INTRAMOLECULAR 1

2-OXIDATION

ELECTRON-TRANSFER

1

3-DIENES

1

4-OXIDATION

CARBOPALLADATION

HETEROANNULATION

TRANSFORMATIONS

NUCLEOPHILES

REAGENT

Chemistry

Kemi

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