Method for synthesizing .beta.-lactones and alkenes

Details Method for synthesizing .beta.-lactones and alkenes Method for synthesizing .beta.-lactones and alkenes

1989-04-26

1991-04-02

Raymond, Richard L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549214, 549332, C07D30512

Patent

active

050048155

ABSTRACT:
.beta.-Lactones are synthesized from a thiol ester and a ketone by a method which efficiently produces .beta.-lactones in high yields. The method involves combining the thiol ester, a ketone or aldehyde, a base, and an organic solvent at subambient temperatures. The thiol ester and ketone form an adduct, which upon warming, spontaneously cyclizes to yield a .beta.-lactone. .beta.-Lactones formed by this method are then decarboxylated, generally by warming in the presence of an adsorbent in an organic solvent, to stereospecifically form the corresponding alkenes.

REFERENCES:
J. Wemple, Tetrahedron Letters No. 38:3225-3258 (1975).
W. Adam and H. Fick, Journal of Organic Chemistry 43(24):4574-4577 (1978).
W. Adam et al., Journal of the American Chemical Society 94:2000-2006 (1972).
D. Seebach and R. Haner, Chemistry Letters, pp. 49-52 (1987).
D. J. Dagli et al., Journal of Organic Chemistry 40:3173-3178 (1975).
W. Adam and L. A. A. Encarnacion, Synthesis, pp. 388-390 (1979).
S. Musamune et al., Journal of the American Chemical Society 98:7874-7875 (1976).

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