Asymmetric epoxidation of allylic alcohols

Details Asymmetric epoxidation of allylic alcohols Asymmetric epoxidation of allylic alcohols

1987-09-14

1988-08-16

Milestone, Norma S.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D30119

Patent

active

047646284

ABSTRACT:
Asymmetric epoxidation of allylic alcohols using carboxylic acid treated phenethyl hydroperoxide oxidate and titanium tartrate catalyst gave optically active glycidols following an enantioselection rule opposite to that observed from the Sharpless epoxidation (U.S. Pat. No. 4,471,130). Overall yield and enantiomeric excess of the glycidol made are dependent on the amount of carboxylic acid present in the oxidate feed. This novel finding provides a direct epoxidation route to (R)-glycidol using the less expensive natural L-(+)-dialkyl tartrate ligand.

REFERENCES:
patent: 3625981 (1971-12-01), Kollar
patent: 3870729 (1975-03-01), Bost et al.
patent: 3928393 (1975-12-01), Herzog
patent: 4471130 (1984-09-01), Katsuki et al.
patent: 4594439 (1986-06-01), Katsuki et al.

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