3-substitutes isoxazolidines as chiral auxiliary agents

Details 3-substitutes isoxazolidines as chiral auxiliary agents 3-substitutes isoxazolidines as chiral auxiliary agents

1998-10-09

2000-02-01

McKane, Joseph K.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D26102

Patent

active

060204974

ABSTRACT:
Disclosed are compounds of the formula: ##STR1## where R is selected from the group consisting of C.sub.1 -C.sub.4 linear or branched alkyl, trifluoromethyl, halo, phenyl, biphenyl and naphthyl, wherein the aromatic group can be substituted with C.sub.1 -C.sub.4 linear or branched alkyl, trifluoromethyl, or halo; and wherein the asterisked 3-position ring carbon is either in (R) or (S) configuration, or racemate form, and salts thereof formula I. The compounds are useful in chiral synthesis, for example, producing naturally occurring L-amino acids, e.g., alanine, from aliphatic acid precursors.

REFERENCES:
patent: 5561178 (1996-10-01), Prabhu
A. Abiko et al., "New Isoxazolidine-based Chiral Auxiliaries for Asymmetric Syntheses," Tetrahedron Letters, Vol. 38, No. 18, pp. 3261-3264, (1997).
A. Abiko et al., "Benzopyranoisoxazolidines as Chiral Auxiliaries for Asymmetric Synthesis," Angew. Chem. Int. Ed. Engl., Vol. 34, No. 7, pp. 793-795 (1995).
Ca 115: 92853z Asymmetric syntheses of . . . cycloaddition. Keirs et al., p. 826, 1991.

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