A Recyclable Organocascade Reaction System: Stereoselective Precipitation of Optically Active cis- Delta d-Lactols with Quaternary Stereocenters during the Michael-Hemiacetalization Reaction
A cascade Michael-hemiacetalization reaction between Delta *b-substituted Delta *b-nitroethanols and , Delta *b-unsaturated aldehydes is described, which provides a convenient and efficient synthesis for cis- Delta *d-lactols with quaternary stereocenters in moderate yields with excellent enantiosel...
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Veröffentlicht in: | Advanced synthesis & catalysis 2010-11, Vol.352 (17), p.2875-2880 |
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Hauptverfasser: | , , , , , , |
Format: | Artikel |
Sprache: | eng |
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Online-Zugang: | Volltext |
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Zusammenfassung: | A cascade Michael-hemiacetalization reaction between Delta *b-substituted Delta *b-nitroethanols and , Delta *b-unsaturated aldehydes is described, which provides a convenient and efficient synthesis for cis- Delta *d-lactols with quaternary stereocenters in moderate yields with excellent enantioselectivity. Based on the selective precipitation of cis- Delta *d-lactols, which were isolated by filtration, the catalytic system in the filtrate can be reused directly and recycled for eight times without any obvious deterioration in enantioselectivity. |
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ISSN: | 1615-4169 |
DOI: | 10.1002/adsc.201000553 |