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Professor Tristan Lambert

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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Jeffrey S Bandar, Tristan H Lambert
Journal of the American Chemical Society 2013-08-14
Cyclopropenimine 1 is shown to catalyze Mannich reactions between glycine imines and N-Boc-aldimines with high levels of enantio- and diastereocontrol. The reactivity of 1 is shown to be substantially greater than that of a widely used thiourea cinchona alkaloid-derived catalyst. A variety of aryl and aliphatic N-Boc-aldimines a...Read More
Jeffrey S Bandar, Tristan H Lambert
Journal of the American Chemical Society 2012-03-28
Cyclopropenimines are shown to be a highly effective new class of enantioselective Brønsted base catalysts. A chiral 2,3-bis(dialkylamino)cyclopropenimine catalyzes the rapid Michael reaction of a glycine imine substrate with high levels of enantioselectivity. A preparative scale reaction to deliver 25 g of product is demonstrat...Read More