AI Article Synopsis
- The study presents a new method using organocatalysis to create complex spiro[2,3]hexane structures from methylenecyclopropanes and various α,β-unsaturated aldehydes.
- The process involves a two-step reaction: a Michael addition followed by the expansion of the cyclopropane ring, with an enamine playing a crucial role in the transformation.
- The effectiveness of this strategy relies on a specific electron-deficient difluoro-substituted secondary amine catalyst and the inherent reactivity of the starting materials.
Article Abstract
We herein report a general organocatalytic enantioselective strategy for the construction of highly strained spiro[2,3]hexane skeletons from methylenecyclopropanes and a broad selection of α,β-unsaturated aldehydes. The reaction proceeds through a Michael addition followed by ring expansion of methylenecyclopropanes and nucleophilic attack of an enamine to realize the construction of spiro[2,3]hexanes. Key to the success of this approach are the utilization of an electron-deficient difluoro-substituted secondary amine catalyst and the intrinsic reactivity of methylenecyclopropanes.
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| http://dx.doi.org/10.1002/anie.201912834 | DOI Listing |
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