Enantioselective Synthesis of Indanes with a Quaternary Stereocenter via Diastereoselective C(sp3)-H Functionalization

A practical synthesis of enantioenriched indane derivatives with quaternary stereocenters was developed via sequential enantioselective reduction and C-H functionalization. Good to excellent enantioselectivity could be achieved by either the CuH-catalyzed asymmetric reduction or the Corey-Bakshi-Shibata (CBS) reduction of indanone derivatives. The subsequent diastereo-specific and regioselective rhodium-catalyzed silylation of the methyl C-H bond led to indane derivatives with quaternary centers. This strategy was further applied in syntheses of (nor)illudalane and botryane sesquiterpenoids.

Automated summary

A practical synthesis of enantioenriched indane derivatives with quaternary stereocenters was developed via sequential enantioselective reduction and C-H functionalization. Good to excellent enantioselectivity could be achieved by either the CuH-catalyzed asymmetric reduction or the Corey-Bakshi-Shibata (CBS) reduction of indanone derivatives. The strategy was further applied in syntheses of (nor)illudalane and botryane sesquiterpenoids.