Size- and shape-selective substrate deuteration catalyzed by a water-soluble synthetic receptor
Anastasia Karavasili1,2, Jose L Moreno3, Grant J Stucky1,4
1Department of Natural Sciences of Pitzer and Scripps Colleges, Claremont, CA 91711, USA. bcaulkins@natsci.claremont.edu.
Abstract:
Encapsulation of cyclic alkanones in a water-soluble deep cavitand enables the selective deuteration of substrates. The biomimetic host can selectively and catalytically α-deuterate cycloalkanones in aqueous solution under mild conditions. The guests can turnover, allowing reaction to occur with as little as 3% cavitand as catalyst, and the process is size-, shape-, site- and carcero-selective; reaction occurs in the cavity alone, and only with protons in close proximity to the cavitand walls.
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