The design of efficient and selective routes to a key 1,4-cis-substituted cyclohexylamide intermediate

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• 作者：Christopher Barfoot ; Gerald Brooks ; David T. Davies ; John Elder ; Ilaria Giordano ; Alan Hennessy ; Graham Jones ; Roger Markwell ; Michael McGuire ; Timothy Miles ; Neil Pearson ; Grant Spoors ; Ravinder Sudi
• 刊名：Tetrahedron Letters
• 出版年：2010
• 出版时间：26 May 2010
• 年：2010
• 卷：51
• 期：21
• 页码：2846-2848
• 全文大小：332 K

文摘

This Letter describes the synthetic challenges in synthesising key 1,4-cis-substituted cyclohexylamide intermediate 1 for our research programme. Five different routes address the major issues of selectivity to afford the cis product in isomerically pure form and in high yield. Major purification issues were also encountered upon scaling some of the routes. The merits of the diverse routes are assessed and the reasoning given for which one was ultimately used for large-scale synthesis of 1.