five

Stereoselective Access to the Versatile 4-Aminohex-5-ene-1,2,3-triol Pattern

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https://figshare.com/articles/dataset/Stereoselective_Access_to_the_Versatile_4_Aminohex_5_ene_1_2_3_triol_Pattern/3312751
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We developed a stereocontrolled route allowing potential access to the eight isomers of 4-benzylaminohex-5-ene-1,2,3-triol in two or four steps and ca. 50% yield from readily available chiral nonracemic cis- or trans-α,β-epoxyimine precursors. A new (NH4)2CO3-based carboxylation/intramolecular cyclization sequence allowed regio- and stereocontrolled C-3 epoxide opening while neat C-2 hydrolysis was ensured by simple aqueous acidic treatment.
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2004-12-10
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