Chiral auxiliaries are important tools in asymmetric synthesis. The Evans auxiliary is considered the benchmark because of its effectiveness in a host of applications including enolate alkylation, aldol and Diels-Alder reactions, and countless natural product and pharmaceutical syntheses. Although remarkably effective, chiral auxiliaries are expensive and not easily recycled. To address these issues, we have developed a novel chiral auxiliary with the following properties: 1) chemically robust, 2) inexpensive, 3) highly crystalline and 4) contains strongly coordinating atoms for Lewis acid promoted reactions. We will report results with a series of sulfonamide auxiliaries to optimize selectivity and yield in enolate alkylation, Diels-Alder, and aldol reactions.

Design of an inexpensive chiral auxiliary for diastereoselective alkylation, aldol and Diels-Alder reactions

251st National Meeting (2016)

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