Process for preparing intermediates for the synthesis of antifun

Details Process for preparing intermediates for the synthesis of antifun Process for preparing intermediates for the synthesis of antifun

1993-04-30

1995-04-04

Lee, Mary C.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D24908

Patent

active

054039371

ABSTRACT:
Disclosed is a process for preparing chiral compounds of the formula (I) ##STR1## wherein: X.sup.1 and X.sup.2 are independently F or Cl; and E is --SO.sub.2 R.sup.2, wherein R.sup.2 is C.sub.1 -C.sub.6 alkyl, --C.sub.6 H.sub.4 CH.sub.3 or --CF.sub.3 ; its enantiomer and racemates thereof, useful in the synthesis of tetrahydrofuran azole antifungals. Novel compounds of the formula ##STR2## wherein: X.sup.1 and X.sup.2 are independently F or Cl; B represents --C(O)Q* or --CH.sub.2 OR"; Q* represents a chiral auxiliary group; R" represents a hydroxy protecting group selected from --CH.sub.2 C.sub.6 H.sub.5, or --C(O)R.sup.1, wherein R.sup.1 is C.sub.1 -C.sub.6 alkyl; and A represents Cl, Br, I or triazolyl; are also disclosed.

REFERENCES:
patent: 5039676 (1991-08-01), Saksena et al.
Evans et al., J. Amer. Chem. Soc., 112, 8215-8216 (1990).
Evans et al., J. Amer. Chem. Soc., 104, 1737-1739 (1982).
Evans et al., J. Amer. Chem. Soc., 113, 1047-1049 (1991), with supplemental material.
Freifelder, Catalytic Hydrogenation in Organic Synthesis, pp. 120-121 (1978).
Oppolzer, et al, J. Amer. Chem. Soc., 112, 2767-2772 (1990).
Evans, et al, J. Amer. Chem. Soc., 103, 2127-2129 (1981).
Evans, et al., Tetrahedron, 44, 5525-5540 (1988).

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