Method for synthesizing oxetan-2-ones and intermediates for thei

Details Method for synthesizing oxetan-2-ones and intermediates for thei Method for synthesizing oxetan-2-ones and intermediates for thei

1998-01-16

1999-05-11

Trinh, Ba K.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D305/12

Patent

active

059028866

ABSTRACT:
A method is described for the synthesis of oxetan-2-ones comprising protection of the hydroxy group of an hydroxy ester with an acid-labile acetal protecting group, reduction of this O-protected hydroxy ester to an O-protected hydroxy aldehyde, condensation of this aldehyde with a metal enolate of an activated carboxylic acid derivative and spontaneous deprotection of the hydroxy group during the acidic workup procedure. Using the new O-protected hydroxy aldehydes as intermediates the oxetan-2-ones can be obtained after separation in diastereomerically and enantiomerically pure form, in a remarkably reduced number of steps, and in a significantly improved overall yield.

REFERENCES:
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S. Hanessian, A.Tehim, P.Chen, J. Org. Chem. 1993, 58, 7768-7781.
I.Fleming, N.J.Lawrence, Tetrahedron Lett., 1990, 31, 3645-3648.
J.J.Landi, L.M. Garofalo, K.Ramig, Tetrahedron Lett., 1993, 34, 277-280.
P. Barbier, F.Schneider, J. Org. Chem., 1998, 53, 1218-1221.

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