A Simpler Route for Making Nitrogen-Alkene Rings

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Science  03 Jan 2014:
Vol. 343, Issue 6166, pp. 33-34
DOI: 10.1126/science.1248166

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Nitrogen is a key component of many natural products and drug molecules. It has been estimated that among all natural products, the average number of nitrogen atoms per molecule is 0.7, while for medicinal drugs, this number rises to 3.0 (1). A versatile method for the synthesis of nitrogen-containing molecules is to use nitrogen-bridged alkenes (aziridines) as building blocks, as the ring strain makes them highly reactive. Aziridines are also present in a number of biologically active natural products (2) (see the figure, panel A). Current aziridination methods (35) almost always require the use of a protecting group on the nitrogen atom. The removal of these groups can sometimes be problematic because of the need for harsh reaction conditions. A direct aziridination method that would circumvent the need to use such a protecting group has so far remained elusive, with few exceptions (68). Thus, practical and direct methods for the preparation of aziridines are very useful. On page 61 of this issue, Jat et al. (9) report the direct synthesis of N-H and N-Me aziridines in a single step and under mild reaction conditions.