Journal
SYNTHESIS-STUTTGART
Volume -, Issue 12, Pages 2040-2046Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-2004-829142
Keywords
1,3-amino alcohols; hydrazones; aldol reaction; nucleophilic addition; N-N bond cleavage
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An efficient diastereo- and enantioselective access to all-syn-configured, differently N,O-protected 1,3-amino alcohols via a titanium tetrachloride mediated aza-enolate aldol reaction/aldehyde hydrazone 1,2-addition protocol is described. The O-TBS and N-Cbz protected title compounds are obtained after reductive N-N bond cleavage in a four steps synthesis with moderate to good overall yields (18-58%), high diastereomeric (de = 78% to greater than or equal to96%) and enantiomeric (ee greater than or equal to96%) excesses.
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