Conversion of optically active epoxy alcohols to allylic alcohol

Details Conversion of optically active epoxy alcohols to allylic alcohol Conversion of optically active epoxy alcohols to allylic alcohol

1989-09-11

1990-06-19

Evans, J. E.

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

549556, C07C 2974, C07C 2900, C07C 3303

Patent

active

049354515

ABSTRACT:
A two step procedure converts an epoxide residue from a Sharpless kinetic resolution of secondary allyl alcohols into an allyl alcohol of the desired chirality. The Sharpless system selectively epoxidizes one enantiomer of the allyl alcohol and leaves the other substantially unreacted. Then the epoxy alcohol is treated with methanesulfonyl anhydride and converted to epoxy mesylate. This product is contacted with a telluride salt in aqueous solution to convert it to the desired allyl alcohol with the chiral center inverted. This technique effects nearly complete conversion of racemic starting material to a single desired enantiomer.

REFERENCES:
patent: 4471130 (1984-09-01), Katsuki et al.
patent: 4594439 (1986-06-01), Katsuki et al.
Polson et al., Functional Group Modification via Organotellurium Chemistry, Tetrahedron Letters, V. 27, p. 5579 (1986).
Discordia et al., 2-Substituted-4-Hydroxymethyltellurophenes, Tetrahedron Letters, V. 29, p. 4923 (1988).
Barton et al., Sodium Hydrogen Telluride as a Useful Nucleophilic Reagent, Tetrahedron Letters, V. 26, p. 6197 (1985).
Clive et al., Alkali Metal O, O-Diethyl Phosphorotelluroates, 45 J. Org. Chemistry 2347 (1980).
Polson et al., Some New 3-Substituted 3-Hydroxyselenetanes, 53 J. Org. Chemistry 791 (1988).

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