A bis-aziridination reaction of a series of allenes was used to prepare a highly unusual class of heterocycles, the 1,4-diazaspiro[2.2]pentanes (DASPs).  Three different synthetic approaches were explored, consisting of intra/intra-, inter/inter-, and intra/intermolecular bis-aziridinations.  The intra/intermolecular formation of DASPs was the most useful due to the high levels of chemo-, regio- and diastereoselectivity achievable using this approach.  Our ability to differentiate between the electronics of the two aziridines of the DASPs allowed us to control the subsequent reactivity of these strained rings with a wide range of nucleophiles and electrophiles.  The use of DASPs as reactive intermediates in a variety of tandem reactions yielded novel stereotriads containing three new contiguous, heteroatom-bearing stereocenters.

Synthesis and reactivity of 1,4-diazaspiro[2.2]pentanes

243rd National Meeting (2012)

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