Tetrahedron p. 8929 - 8940 (1994)
Update date:2022-08-11
Topics:
Dussault, Patrick H.
Woller, Kevin R.
Hillier, Michael C.
The auxiliary-directed reaction of singlet oxygen with tiglate esters furnishes an asymmetric synthesis of 3-hydroperoxy-2-methylidene butenoates. Although previous reports have suggested that s-cis enoate conformers undergo preferential oxygenation relative to the s-trans conformers, our results suggest that both conformers are reactive and that the modest stereoselectivity is based upon a conformational equilibrium favoring the s-trans conformer.
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