Hydrogen-bonding catalysts are an emerging and promising source of organocatalysts that have proven to be important in biological systems and are making their way into natural product syntheses. These small molecule metal-free catalysts are receiving increased attention due to their relatively simple and inexpensive syntheses and their environmentally friendly nature. The catalytic performance of these compounds has been shown to be dependent on their acidities, which is one reason Schreiner’s catalyst [(3,5-(CF3)2C6H3NH)2CS] is considered to be the most effective thiourea hydrogen bond catalyst. Previously, professor Kass’s group developed positively-charged thiourea catalysts, which were orders of magnitude more reactive than Schreiner’s thiourea. These species were also found to be useful in asymmetric transformations such as the Fridel-Craft alkylation of indole with <i>trans</i>-b-nitrostyrene. Computational modeling of this transformation suggested that the introduction of a tert-butyl group into the catalyst will improve its activity and enantioselectivity. Therefore, this project aims to synthesize the necessary aminoindanol and convert it to the modified thiourea so that its catalytic performance can be evaluated.

Synthesis and reactivity of charge-enhanced chiral thiourea catalysts

2019 Spring National Meeting

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.