One of the main strategies for the synthesis of enantiopure compounds is based on the utilization of chiral auxiliaries.[1] Transformations tend to be versatile, proceed with a predictable sense of asymmetric induction and lead to products in enantiomerically enriched form. The (-)-8-phenylmenthol auxiliary, one of the most successful and popular examples, has been used to afford good diastereoselectivity in numerous organic transformations. However (-)-8-phenylmenthol has many drawbacks: it is expensive, not very modular, and its synthesis is not straightforward. Moreover, its enantiomer, (+)-8-phenylmenthol is even less available.<br/>That is why we synthesized a new auxiliary, designed on a conformationally restricted version of (-)-8-phenylmenthol, in both enantiomeric forms on multigram scale.[2] A first application has already shown comparable diastereoselectivity between the novel auxiliary and (-)-8-phenylmenthol.<br/>We want to present an improved synthesis of this auxiliary and an extension of the platform to new auxiliaries.<br/>

New improvements in the synthesis tetralol-related chiral auxiliaries

251st National Meeting (2016)

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