Expansion of Thiele鈥檚 Acid Chemistry in Pursuit of a Suite of Conformationally Constrained Scaffolds

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• 作者：Jun Chen ; Brenden Kilpatrick ; Allen G. Oliver ; Jeremy E. Wulff
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：September 18, 2015
• 年：2015
• 卷：80
• 期：18
• 页码：8979-8989
• 全文大小：608K
• ISSN：1520-6904

文摘

The Diels鈥揂lder dimer of cyclopentadiene carboxylate, Thiele鈥檚 acid has conformational properties that make it attractive as a molecular scaffold for applications in supramolecular and biological chemistry. However, a lack of known reaction methodology for derivatives of Thiele鈥檚 acid (or the corresponding esters) has hampered its utilization in these fields. We describe an improved preparation of Thiele鈥檚 esters and survey the chemistry of these versatile intermediates. As part of this effort, we also describe the synthesis of a suite of Thiele鈥檚 acid (or ester) analogues spanning a broad range of cleft angles.