Abstract
Chiral sulfinyl groups have been widely used in organic synthesis as a stereo- and enantiodirecting functionality and the high efficiency of the selectivity has received much attention in recent years. In this review we wish to cover the work published in the literature since 1996. The participation of a chiral sulfinyl function in a wide range of reactions as well as the application of these methodologies to the synthesis of natural products are reported.
Highlights
Over the two last decades, chiral three coordinate sulfur compounds have received considerable attention as key intermediates in asymmetric synthesis[1] or as pharmaceutical goals.[2]
Use of the sulfinyl group as chiral auxiliary in stoichiometric stereoselective reactions. This area has lately received a lot of attention in asymmetric synthesis as a great number of stereoselective transformations involving sulfoxides have been described in the chemical literature
Chemical asymmetric desymmetrisation of prochiral diols using chiral sulfoxides has been studied extensively over tje last decade by Iwata et al They first established that synthetically useful chiral building blocks such as enantiomerically pure 1,2 or 1,3-diols can be obtained via diastereoselective β-elimination of chiral α-sulfinyl acetals.[64]
Summary
Over the two last decades, chiral three coordinate sulfur compounds have received considerable attention as key intermediates in asymmetric synthesis[1] or as pharmaceutical goals.[2]. The first one deals with the stereoselective generation of new stereogenic centres using a chiral sulfinyl group as auxiliary. The asymmetric transformation of the chiral sulfinyl group leading to new stereogenic centres will be described in the last section. Use of the sulfinyl group as chiral auxiliary in stoichiometric stereoselective reactions This area has lately received a lot of attention in asymmetric synthesis as a great number of stereoselective transformations involving sulfoxides have been described in the chemical literature. Few conceptually new methods have been developed, we have selected only recent insights of generally well-established methodologies. This part is divided in several sections related to the sulfinyl-containing reactive species involved in stoichiometric diastereoselectives transformations
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