Prof. Tristan Lambert and his co-coworkers have developed a new class of highly effective chiral Brønsted base catalysts, formulated from the unique cyclopropenimine architecture. As shown by Lambert, cyclopropenimines have basicities that significantly surpass that of many common organic bases, such as BTMG or DBU, and rival those of the P1 phosphazene superbases. The catalysts designed by Lambert have a finely-tuned basicity, however, which makes the generation of the base from its conjugate acid operationally simple (no NaH or nBuLi) and provides maximal catalytic turnover rates. The first generation chiral cyclopropenimine catalyst (L511188) thus offers reactivity enhancements of nearly three orders of magnitude over alternative catalysts, and is available for a fraction of the cost.
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