Optically active enantiomers of substituted glyceraldehydes or g

Details Optically active enantiomers of substituted glyceraldehydes or g Optically active enantiomers of substituted glyceraldehydes or g

1991-06-18

1992-11-10

Raymond, Richard L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549214, 549229, 549230, 549350, C07D41104

Patent

active

051625547

ABSTRACT:
Stable, optically active enantiomers of substituted glyceraldehydes or glycidaldehydes are synthesized by using osmium-catalyzed asymmetric dihydroxylation of an olefin which is a substituted 1,5-dihydro-3H-2,4-benzodioxepine. For example, the protected glyceraldehyde, 3-(1,2-dihydroxyethyl)-1,5-dihydro-3H-2,4-benzodioxepine and the protected glycidaldehyde, 3-(1,2-epoxyethyl)-1,5-dihydro-3H-2,4-benzodioxepine have been synthesized and the optical enantiomer has been recovered. In the synthetic and isolation methods, enantiomers with high enantiomeric excess are recovered from the mother liquor following a recrystallization step.

REFERENCES:
Hertel et al., Synthetic Comm. 21(2) 151-154 (1991).
N. Machinaga et al., Tet. Letters, "1,5-Dihydro-3H-2,4 benzodioxepine as a novel carbonyl protecting group," 30(31) pp. 4165-4168 (1989).
H. Patney, Tet. Letters, "Sulfonated charcoal, a mild and efficient reagent for the preparation of cyclic acetals . . . " 32(3) pp. 413-416 (1991).
K. Sharpless, et al., J. Org. Chem., "Rapid Separation of organic mixtures by formation of metal complexes," 40(9), pp. 1252-1257 (1975).
J. Jurezak et al., Tetrahedron, "(R)-and (S)-2,3-O-isopropylideneglyceraldehyde in stereoselective organic synthesis," 42(2) pp. 442-488 (1986).

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