Ketenimine mediated synthesis of lactam iminosugars: development of one-pot process via tandem hydrative amidation of amino-alkynes and intramolecular transamidation

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• 作者：Inderpreet Arora ; Arun K. Shaw ; ^{akshaw55@yahoo.com" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Amidation ; Iminosugar ; Ketenimine ; Lactams ; N-heterocycles
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：1 September 2016
• 年：2016
• 卷：72
• 期：35
• 页码：5479-5487
• 全文大小：993 K

文摘

Cu-catalysed ketenimine mediated multicomponent reaction led to an efficient installation of N-allyl N-sulfonyl amide functionality onto a sugar derived terminal alkyne via intramolecular 3,3 sigmatropic rearrangement of an initially formed N-sulfonyl imidate. This strategy is further extended to the application of hydrative amide synthesis on chiral alkynyl amines followed by in situ intramolecular transamidation which led to the development of a novel one-pot reaction for the construction of a δ-lactam iminosugar.