- [3,3]-Sigmatropic Rearrangements in the Enantioselective Synthesis of (-)-Methylenolactocin
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A Pd(II)-catalyzed [3,3]-sigmatropic rearrangement is used to transfer chirality from an enantio-enriched alk-3-ene-1,2-diol to a C2- symmetrical alk-2-ene-1,4-diol which, in turn, can be converted into a precursor of (-)-methylenolactocin through an additional [3,3]-sigmatropic rearrangement (either Johnson orthoester or Ireland-Claisen rearrangement).
- Ariza, Xavier,Fernández, Natalia,Garcia, Jordi,López, Marta,Montserrat, Laia,Ortiz, Jordi
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- A concise synthesis of (-)-methylenolactocin and (-)- phaseolinic acid from (6S,9S)-tetradec-7-yne-6,9-diol
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A novel, stereodivergent route to paraconic acids from C2-symmetric trans- and cis-alk-2-ene-1,4-diols through Ireland-Claisen and/or Johnson orthoester rearrangements is disclosed. This strategy has been applied to the synthesis of (-)-methylenolactocin and (-)-phaseolinic acid from a single chiral diol.
- Ariza,Garcia,López,Montserrat
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- Unsaturated syn - And anti -1,2-amino alcohols by cyclization of allylic bis-trichloroacetimidates. Stereoselectivity dependence on substrate configuration
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Disubstituted allylic bis-imidates undergo Lewis acid catalyzed or spontaneous cyclization to oxazolines, which are precursors of unsaturated amino alcohols. Stereoselectivity of the cyclization is mainly determined by the substrate configuration. Highly
- Grigorjeva, Liene,Kinens, Artis,Jirgensons, Aigars
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