The Synthesis of Chiral Sulfoxides through Nucleophilic Displacement at Sulfur

THE SYNTHESIS OF CHIRAL SULFOXIDES THROUGH NUCLEOPHILIC DISPLACEMENT AT SULFUR 

2 The Andersen procedure for the synthesis of ENANTIOMERICALLY ENRICHED, CHIRAL SULFOXIDES 41 

The use of sulfoxides as chiral synthons has, over recent years, become a highly dependable protocol in synthetic organic chemistry. To some extent, however, the use of sulfoxides in asymmetric synthesis has been limited by the lack of a reliable and general method for their preparation in optically pure form. In this review we present the development of chiral sulfoxide synthesis via nucleophilic displacement at sulfur from the pioneering work of Andersen in 1962 to more recent methods. Sulfoxides have become associated with many diverse areas of synthetic chemistry indeed, their ability to act as a handle for the stereoselective generation of chirality at proximate centres has attracted much research worldwide. 

2 The Andersen Procedure for the Synthesis of Enantiomerically Enriched, Chiral Sulfoxides 

Following the pioneering work of Gilman [1], Andersen, in 1962, reported the first synthesis of an optically active sulfoxide of high enantiomeric purity through nucleophilic displacement at sulfur [2]. The key step in Andersen s procedure 

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