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.
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| http://dx.doi.org/10.1021/ol202588g | DOI Listing |
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