Bis-Lewis acids-catalyzed highly diastereoselective one-pot reductive dehydroxylation of chiral N,O-acetals

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• 作者：Li-Jiao Jiang ; Bo Teng ; Jian-Feng Zheng ; Jian-Liang Ye ; Pei-Qiang Huang
• 关键词：Cooperative effects ; Diastereoselectivity ; Lewis acids ; Asymmetric synthesis ; Heterocycles
• 刊名：Tetrahedron
• 出版年：2010
• 出版时间：2 January 2010
• 年：2010
• 卷：66
• 期：1
• 页码：172-175
• 全文大小：303 K

文摘

A one-pot and highly diastereoselective method for the reductive dehydroxylation of three classes of heterocyclic N,O-acetals with general structure 4 is reported. The method features a ‘two in one’ concept, namely, by synergetic action of two complementary Lewis acids (BF·OEt₂ and TiCl₄), the bicyclic or tricyclic oxazololactams 5 were formed in situ and reductively cleaved to give the corresponding lactams 6 in a high-yielding and highly diastereoselective manner.