Process for preparing chiral sulphoxides

Details Process for preparing chiral sulphoxides Process for preparing chiral sulphoxides

1990-09-28

1991-11-26

Prescott, Arthur C.

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

Organic compounds

Heavy metal containing

556 15, 556 31, 556145, C07F 1502

Patent

active

050683691

ABSTRACT:
A process for preparing single enantiomers of chiral sulphoxides is provided. The process involves (a) reacting an achiral sulphur-containing compound, 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 stereospecifically 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:
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patent: 3966783 (1976-06-01), Suschitzky et al.
patent: 4036983 (1977-07-01), Rutherford et al.
patent: 4118509 (1978-10-01), Lattrell et al.
Pitchen et al., "An Efficient Asymmetric . . . ", J. Am. Chem. Soc. 1984, 106, pp. 8188-8193.
Di Furua et al., "Synthesis of Chiral Sulphoxides . . . ", Communications, Apr. 1984, pp. 325-326.
Hwang et al., "Total Synthesis of (+) . . . ", J. Org. Chem., 1985, 50, 1264-1271.
Flood et al., "Preparation, Resolution . . . ", Abstract #631441, Organometallics, vol. 85, 1976, p. 573.
Weber, "A Carbonlyliron-Containing Sulphur Ylide", Chemical Abstracts, vol. 86, 1977, #89989a, p. 562.

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