Oxo-Diels–Alder reaction

Oxo-Diels–Alder reaction
Named after Otto Diels
Kurt Alder
Reaction type Cycloaddition
Identifiers
RSC ontology ID RXNO:0000310

An oxo-Diels–Alder reaction (also called an oxa-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.

See also

References

  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
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