title: Expansion of Thiele's Acid Chemistry in Pursuit of a Suite of Conformationally Constrained Scaffolds.
abstract: The Diels-Alder dimer of cyclopentadiene carboxylate, Thiele's 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's acid (or the corresponding esters) has hampered its utilization in these fields. We describe an improved preparation of Thiele's esters and survey the chemistry of these versatile intermediates. As part of this effort, we also describe the synthesis of a suite of Thiele's acid (or ester) analogues spanning a broad range of cleft angles.
authors: Department of Chemistry, University of Victoria , P.O. Box 3065 STN CSC, Victoria, BC V8W 3V6, Canada.
authors: Jun
authors: J
authors: Chen
authors: Department of Chemistry, University of Victoria , P.O. Box 3065 STN CSC, Victoria, BC V8W 3V6, Canada.
authors: Brenden
authors: B
authors: Kilpatrick
authors: Molecular Structure Facility, Department of Chemistry and Biochemistry, University of Notre Dame , 251 Nieuwland Science Hall, Notre Dame, Indiana, 46556, United States.
authors: Allen G
authors: AG
authors: Oliver
authors: Department of Chemistry, University of Victoria , P.O. Box 3065 STN CSC, Victoria, BC V8W 3V6, Canada.
authors: Jeremy E
authors: JE
authors: Wulff