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Amino alcoholsQ 0240 Stereocontrolled Synthesis of β-Amino Alcohols from Lithiated Aziridines and

Boronic Esters. — A conceptionally new route to β-amino alcohols employs the trap-ping of lithiated 2-alkyl N-Boc aziridines with boronic esters to give the syn-products (III) with complete diastereoselectivity. The process is easily extended to the enantio-riched series with complete dia- and enantioselectivity and without any matched/mis-matched issues. In the case of 2-phenyl aziridines, the use of Bus-protected analogue (VII) is preferred to avoid the known migration of the Boc protecting group to the 2-po-sition during the lithiation process. In dependence on the sterical hindrance of the base used, either the secondary amino alcohols (VIII) or the quaternary analogues (IX)/(XI) can be prepared. — (SCHMIDT, F.; KELLER, F.; VEDRENNE, E.; AGGARWAL*, V. K.; Angew. Chem., Int. Ed. 48 (2009) 6, 1149-1152; Dep. Chem., Univ. Bristol, Cantock's Close, Bristol BS8 1TS, UK; Eng.) — Kieslich

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ChemInform 2009, 40, issue 22 © 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

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ChemInform 2009, 40, issue 22 © 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim