Journal
ORGANIC LETTERS
Volume 7, Issue 16, Pages 3593-3595Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol051456u
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- NIGMS NIH HHS [R01 GM 068650-01A1] Funding Source: Medline
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In this Letter, it is demonstrated that the unusual reactivity of cyclopropenes can increase the scope and utility of intermolecular Paulson-Khand reactions. The well-defined chiral environment of cyclopropenes has a powerful influence on the diastereoselectivity of the reactions and leads to the production of a single cyclopentenone in each of the described cases. The cyclopropane ring strongly influences the stereochemistry of reactions at the enone, and the three-membered ring can subsequently be cleaved under mild conditions.
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