Tetrahedron p. 2195 - 2210 (1991)
Update date:2022-07-30
Topics: Hydrolysis Asymmetric Sharpless Epoxidation Regioisomeric Divinylcarbinol Erythro-Dand -L-4-pentenitols
Jaeger, Volker
Schroeter, Detlef
Koppenhoefer, Bernhard
The asymmetric Sharpless epoxidation of divinylcarbinol (1), a secondary, achiral allylic alcohol, is described in detail.The epoxidation proceeds with high enantio-control and diastereo-selection.The resulting 1,2-epoxy-4-pentene-3-ols 2 are equilibrated to afford the internal epoxides 5.Hydrolysis of the regioisomers 2 and 5, respectively, furnishes opposite enantiomers of erythro-4-pentenitols 3 with high selectivity.Several derivatives of 3 are described, as well as result of a less stereoselective route - from D-glyceraldehyde acetonide (10) - providing NMR data of the threo series. - The acute toxicity of divinylcarbinol (1) is reported, along with the mutagenicity of 1, L-2 and L-5 as determined by Ames tests.
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