Abstract
Publisher Summary This chapter discusses asymmetric synthesis from β-keto sulfoxides and analogues, largely excluding α-sulfinyl carbanions. The Andersen method for homochiral sulfoxide preparation is reviewed in detail, as well as the asymmetric reduction of β-keto sulfoxides and Diels-Alder additions of vinylic β-keto sulfoxides and analogues. Several applications for the total synthesis of natural products are also described. One of the great advantages of chiral sulfoxides in total synthesis is to allow the asymmetric induction step to occur in the very last part of the synthesis through the stereoselective β-keto sulfoxide reduction. Furthermore, both configurations of the chiral hydroxylic centre can be prepared according to the reduction conditions—Diisobutylaluminium hydride (DIBAL) or ZnCl 2 /DIBAL— allowing the obtainment of both enantiomers of the target molecule. The asymmetric synthesis of two macrolides using the stereoselective reduction of β-keto sulfoxides is recently reported.
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