Benzaldehyde intermediates useful in the preparation of 7-oxabic

Details Benzaldehyde intermediates useful in the preparation of 7-oxabic Benzaldehyde intermediates useful in the preparation of 7-oxabic

1994-05-20

1995-07-25

Daus, Donald G.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548236, C07D49308

Patent

active

054363470

ABSTRACT:
A method is provided for preparing a chiral benzaldehyde of the structure ##STR1## by acylating an anhydride of the structure ##STR2## with a chiral oxazolidine of the structure ##STR3## where Q is MgHal or Li, and X, Y and Z are as described herein, to form a keto acid which is reduced and cyclized. The resulting benzaldehyde may be used in making the final anti-thrombotic--anti-vasospastic compounds. Novel intermediates are also provided.

REFERENCES:
patent: 3974173 (1976-08-01), Kelly
patent: 5100889 (1992-03-01), Misra et al.
Agami, C. et al "Kinetic Control of Asymmetric Induction During Oxazolidine Formation from (-) -Ephedrine and Aromatic Aldehydes", Tetrahedron vol. 41, No. 3, pp. 537-540, (1985).
Takahashi, H. et al "A New Asymmetric Synthesis of (R)- and (S)-3-Arylphthalides: Extremely High Diastereoselective Reaction of Arylcarbaldehydes with Chiral [2-(1,3-Oxazolidin-2-yl)phenyl]titanium Ate Complexes", Synthesis pp. 681-682, Jul. 1992.

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