The cobalt catalyzed hydroacylation of 2-allyl-4-pentenals has been developed to form cyclobutanones selectively. This catalyst system favors the formation of the more strained 4-membered ring over the less strained 5-membered ring. Mechanistic studies suggest a low valent cobalt active catalyst. This chemistry has been extended to form trans-fused hydrindanones selectively, which are an important and reoccurring motif in natural products. Furthermore, the cycloisomerization of 2-allyl-4-pentenals has been studied computationally, to discover an unusual induced fit mechanism. With the detailed knowledge of the mode of action in hand, new catalyst systems have been designed in-silico.

Design principles in catalysis: Cobalt-catalyzed cycloisomerizations and in-silico catalyst design

2019 Spring National Meeting

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