Oxo-Diels–Alder reaction

An oxo-Diels–Alder reaction is an organic reaction and a variation of the Diels–Alder reaction in which a suitable diene reacts with an aldehyde to form a dihydropyran ring. This reaction is of some importance to synthetic organic chemistry.

The oxo-DA reaction was first reported in 1949 ^[1] using a methylpentadiene and formaldehyde as reactants.

Asymmetric oxo-DA reactions (including catalytic reactions) are well known.^[2] Many strategies rely on coordinating a chiral Lewis acid to the carbonyl group.

References

^ A Diels–Alder Type Reaction with Formaldehyde Thomas L. Gresham, Thomas R. Steadman J. Am. Chem. Soc., 1949, 71 (2), pp 737–738 doi:10.1021/ja01170a101
^ Tetrahedron Report number 869 Asymmetric hetero-Diels–Alder reactions of carbonyl compounds Helene Pellissier Tetrahedron 65 (2009) 2839–2877 doi:10.1016/j.tet.2009.01.068

[1] A Diels–Alder Type Reaction with Formaldehyde Thomas L. Gresham, Thomas R. Steadman J. Am. Chem. Soc., 1949, 71 (2), pp 737–738 doi:10.1021/ja01170a101

[2] Tetrahedron Report number 869 Asymmetric hetero-Diels–Alder reactions of carbonyl compounds Helene Pellissier Tetrahedron 65 (2009) 2839–2877 doi:10.1016/j.tet.2009.01.068

[1]

[2]

See also

References