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

ABSTRACT: 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.

SUBMITTER: Hernandez-Toribio J

PROVIDER: S-EPMC3229331 | biostudies-literature | 2011 Nov

REPOSITORIES: biostudies-literature

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

Hernández-Toribio Jorge J Hussain Mahmud M MM Cheng Kevin K Carroll Patrick J PJ Walsh Patrick J PJ

Organic letters 20111025 22

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. ...[more]

PMID: 22026754

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