Evidence for Atropisomerism in Polycyclic γ-Butenolides: Synthesis,Scope, and Spectroscopic Studies |
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Authors: | Debayan Roy Dr Beeraiah Baire |
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Institution: | Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600036 Tamil Nadu India |
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Abstract: | Design and development of a domino cyclative approach for the synthesis of new polycyclic γ-butenolides from β-aryl-Z-enoate propargylic alcohols, through the interception of an intermediate of the Z-enoate-assisted Meyer–Schuster rearrangement, has been reported. A systematic NMR analysis of various derivatives of this class revealed and supported the potential atropisomerism associated with them. These molecules represent first examples of butenolide ring-based atropisomeric compounds in organic chemistry. The synthetic process involves a synchronous construction of both rings with concurrent creation of the potential stereogenic rotational axis. |
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Keywords: | atropisomerism butenolides domino cyclization Meyer–Schuster rearrangement propargylic alcohols |
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