An Asymmetric Intramolecular Rauhut-Currier Reaction Initiated by Chiral Selenolate-BINOL Complexes

Abstract

This work reports the new method of Rauhut-Currier reaction (RC) with the use of lithium selenolates, which provided up to 80% yield in a non-asymmetric IRC reaction. Therefore, our paper involves the search for an efficient chiral additive in the asymmetric version. The influence of various reaction parameters, such as solvent, additives, temperature, and time, was examined. The results for the non-asymmetric version were significantly higher with the presence of water, but surprisingly different observations were obtained in the asymmetric version. Here, the chiral scandium complex with tertiary amine played an important role. The reaction carried out in the presence of chiral complexes gave the expected product with up to 60% yield and up to 70% ee.