Process for preparing chiral sulphoxides

Details Process for preparing chiral sulphoxides Process for preparing chiral sulphoxides

1989-02-17

1991-02-05

Ceperley, Mary E.

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

Organic compounds

Sulfur containing

556 16, 556 30, C07C31504

Patent

active

049906763

ABSTRACT:
A process for preparing single enantiomers of chiral sulphoxides is provided. The process involves (a) reacting an achiral sulphur-containing, e.g. a disulphide, with a single enantiomer of a chiral template having the formula T--(CO)--CH.sub.2 R.sup.1, wherein T is suitably (eta.sup.5 --C.sub.5 H.sub.5)Fe(CO)(PPh.sub.3)-- (Ph=phenyl) and (b) thereafter sterospecifically oxidizing the sulphur atom with an oxidizing agent. A single enantiomer of the chiral sulphoxide can then be generated by reacting the oxidized product with a carbanion. In a preferred embodiment the reaction mixture is thereafter treated with further achiral sulphide to provide a process which is catalytic on the chiral template.

REFERENCES:
patent: 3280017 (1966-10-01), Hubel et al.
D. Hwang et al., J. Org. Chem. (1985), vol. 50, pp. 1264-1271.
T. Flood et al., Chem. Abstracts, vol. 85, No. 63144a (1976).
L. Weber, Chem. Abtracts, vol. 86, No. 89989a (1977).
Pitchen, P. et al., "An Efficient Asymmetric . . . " J. Am. Chem. Soc. 1984 106, pp. 8188-8193.
Di Furia, R., et al., "Synthesis of Chiral Sulphoxides . . . " Communications, Apr. 1984, pp. 325-326.

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