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
Hauptverfasser: Zhang, Fanglin, Wei, Mohui, Dong, Junfang, Zhou, Yirong, Lu, Dengfu, Gong, Yuefa, Yang, Xiangliang
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Sprache:eng
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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.
ISSN:1615-4169
DOI:10.1002/adsc.201000553