Stereodivergent total asymmetric synthesis of polyhydroxylated pyrrolidines via tandem allylic epoxidation and intramolecular cyclization reactions
摘要:
Epoxidation of the allylic alcohols 10 and 11 using the VO(acac)2/t-BuOOH system followed by an intramolecular 5-exo cyclization of the resulting δ-epoxycarbamates 12, 13, 18, and 19 has been shown to provide a general and efficient solution for the asymmetric synthesis of polyhydroxy pyrrolidines. The requisite vicinal amino alcohol functionality was enantio-/regio-selectively installed by the Os-catalyzed asymmetric aminohydroxylation reaction of the designed achiral olefin 6.
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关键词:
Polyhydroxylated pyrrolidines Regioselective asymmetric aminohydroxylation Allylic epoxidation Intramolecular cyclization
DOI:
10.1016/j.tetlet.2004.06.048
被引量:
年份:
2004
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