Method for preparing intermediates for the synthesis of steroid

Details Method for preparing intermediates for the synthesis of steroid Method for preparing intermediates for the synthesis of steroid

1990-04-11

1992-02-18

Shah, Mukund J.

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

Organic compounds

Silicon containing

560 20, 560106, 560254, 568 28, 568 31, 568 32, 568 34, 568 35, C07C31502, C07C31504

Patent

active

050896474

ABSTRACT:
This invention provides a novel method for the preparation of optically active arylalykylsulfone derivatives, having a chiral center in the alkyl moiety in either the (R)- or the (S)-configuration. These optically active sulfones find use in the stereospecific synthesis of steroid or vitamin D compounds having chiral center at either carbon 24 or carbon 25 of the side chain. The method comprises the steps of reacting an optically active sulfinate ester having a chiral center at sulfur with a racemic alkyl Grignard reagent to obtain a mixture of diastereomeric sulfoxides, separating the mixture of diastereomeric sulfoxides, and oxidizing separately each of the diastereomers to obtain the desired optically active sulfone.

REFERENCES:
Perlman et al., J. Chem. Soc. Chem. Commun., (16), pp. 1113-1115 (1989).
Fieser, Reagents for Organic Synthesis, vol. 3, p. 194 (1972).
Morrison and Boyd, Organic Chemistry, 4th ed. (1983), p. 159.
Axelrod, J. Am. Chem. Soc. 90, p. 4385 (1968).
Solladie, Synthesis 8, p. 185 (1981).
Solladie, Chimia 48, 233 (1984).
Drabowicz, J. Org. Chem. 47, p. 3325 (1982).

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