Stereoselective vinylogous Mannich reaction of 2-trimethylsilyloxyfuran with N-gulosyl nitrones
摘要：
Stereoselective vinylogous Mannich reaction of 2-trimethylsilyloxyfuran withl-gulose-derived chiral nitrones in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate was investigated. The selectivity was strongly influenced by the bulkiness of theC-substituent of the nitrone: for example,C-benzyloxymethyl nitrone afforded four stereoisomers, whereas bulkyC-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]nitrone gave a single stereoisomer. The latter product was elaborated to afford key synthetic intermediates for polyoxin C and dysiherbaine.
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DOI：
10.1039/c1ob06067h
被引量：
年份：
2011
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