Novel transformation of α,β-unsaturated aldehydes and ketones into γ-amino alcohols or 1,3-oxazines via a 4 or 5 step, one-pot sequenceElectronic supplementary information (ESI) available: Experimental details, characterisation data, ReactIR, 1H and 13C NMR and crystallographic data in CIF format. CCDC 896882. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c2cc36129a

An efficient, 4-step, one-pot, highly stereoselective route to γ-amino alcohols has been developed via an in situ α,β-unsaturated imine formation, β-boration, reduction (C&z.dbd;N) and oxidation (C-B) sequence and especially for certain water-soluble γ-amino alcohols, a further step can be added...

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Hauptverfasser: Calow, Adam D. J, Batsanov, Andrei S, Fernández, Elena, Solé, Cristina, Whiting, Andrew
Format: Artikel
Sprache:eng
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Zusammenfassung:An efficient, 4-step, one-pot, highly stereoselective route to γ-amino alcohols has been developed via an in situ α,β-unsaturated imine formation, β-boration, reduction (C&z.dbd;N) and oxidation (C-B) sequence and especially for certain water-soluble γ-amino alcohols, a further step can be added to directly access the corresponding 1,3-oxazine derivatives. An efficient, 4-step, one-pot, highly stereoselective route to γ-amino alcohols has been developed via an in situ α,β-unsaturated imine formation, β-boration, reduction (C&z.dbd;N) and oxidation (C-B) sequence and for water-soluble products, a further step directly accesses 1,3-oxazine derivatives.
ISSN:1359-7345
1364-548X
DOI:10.1039/c2cc36129a