Chiral, optically active compounds useful as protective groups f

Details Chiral, optically active compounds useful as protective groups f Chiral, optically active compounds useful as protective groups f

1982-12-06

1985-02-05

Chan, Nicky

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549459, 2604537, 560 60, 560147, 568324, 568 67, 568810, 568808, 562512, 564303, 564304, C07D31194, C07D30793

Patent

active

044979606

ABSTRACT:
The invention declares new chiral, optically active compounds of the general formula ##STR1## wherein a 5 or 6 membered lactol ring (E), with X and Y meaning (CR.sup.1 R.sup.2).sub.n, with n=0 to 2 and R.sup.1, R.sup.2 =H, lower alkyl or aryl in any combination which does not impair the anomeric selectivity of I in forming acetals, is fused in a stereospecific manner to a bicyclo[2.2.1]heptane ring system, with A,B,C,D meaning H or methyl in any combination, preferably a bornan ring system, and wherein W has the meaning of H, substituted or unsubstituted alkyl or cycloalkyl or the ring system itself, preferably H, and lower alkyl; and in the case of W=H its anhydro compound of the general formula ##STR2## with A,B,C,D,X,Y and n having the same meaning as in the hydrated form, processes for their preparation and use of these new compounds for the protection of --OH, --SH, --NH-- functions, for racemic resolution, for the preparation of optically active imidoester chlorohydrates as well as of optically active esters, for the preparation of optically enriched alcohols and for the preparation of optically active compounds via asymmetric induction.

REFERENCES:
patent: 4159258 (1979-06-01), Ohloff et al.
patent: 4438023 (1984-03-01), Skorianetz et al.
Hertli et al., Helv. Chim. Acta, 64, 25 (1981).
Miller et al., Tetrahedron Lett., 37, 3347 (1974).

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