Diastereoselective aziridination of 2-B(pin)-substituted allylic alcohols: an efficient approach to novel organoboron compounds.

We report that 2-B(pin)-substituted allylic alcohols are good substrates for diastereoselective aziridinations in the presence of PhI(OAc)(2) and N-aminophthalimide. Under the aziridination conditions, the valuable B-C bond remains intact, affording a variety of novel boron-substituted aziridines in good yields and excellent diastereoselectivities. Oxidation of the aziridine B-C bond enables generation of syn-1,3-aminohydroxy-2-ketones with high diastereoselectivity.