Chiral 3-hydroxypyrrolidin-2-ones from a Baylis??????Hillman adduct: convergent, stereoselective synthesis of a glycosidase inhibitor

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• 作者：Galeazzi ; Roberta ; Martelli ; Gianluca ; Mobbili ; Giovanna ; Orena ; Mario ; Rinaldi ; Samuele
• 刊名：Tetrahedron: Asymmetry
• 出版年：2004
• 出版时间：October 18, 2004
• 年：2004
• 卷：15
• 期：20
• 页码：3249-3256
• 全文大小：346 K

文摘

The O-silyl derivative 4b, prepared starting from the BaylisaaaHillman adduct 4a, underwent cyclization on treatment with (S)-phenylethylamine, to give to an equimolar mixture of the 4,5-cis-disubstituted pyrrolidin-2-ones 9 and 10, exclusively, which after separation by silica gel chromatography were both converted into the 3-hydroxy-4-hydroxymethylpyrrolidine 1 a glycosidase inhibitor.