Asymmetric hetero-Diels–Alder reaction catalyzed by dirhodium(II) carboxamidates

AUTOR(ES)

Doyle, Michael P.

FONTE

National Academy of Sciences

RESUMO

Chiral dirhodium(II) carboxamidates are highly efficient catalysts for reactions between a variety of aldehydes and activated dienes. Catalyst loadings as low at 0.01 mol % have been realized with enantioselectivities up to 97%. Kinetic investigations reveal a pronounced electronic influence on the rate of the hetero-Diels–Alder reaction with a Hammett ρ value of +1.9 (versus σ+). Inhibition of the catalyst by reactant aldehyde is apparent, but reactions show first-order dependence on aldehyde and diene, and there is a variable dependence on catalyst.

Documentos Relacionados

• Hetero Diels-Alder adduct formation between nitrosobenzene and tetra-methyl purpurogallin and its retro-Diels-Alder reaction
• Enantioselective Diels–Alder reactions catalyzed by hydrogen bonding
• The Diels-Alder reaction: an update
• Air-stable, storable, and highly efficient chiral zirconium catalysts for enantioselective Mannich-type, aza Diels–Alder, aldol, and hetero Diels–Alder reactions
• About the synthesis of furanoheliangolides through the Diels-Alder reaction