When ketones flanked on both sides by nucleophilic atoms react with Seebach's nitropropenyl pivaloate reagent, direct couplings take place to give two new ring systems and three bonds. Cis-ring fusions are observed in unions leading to 5,5-, 5,6-, and 6,6-bicycles. Densely functionalized and rigid frameworks may be rapidly formed by the chemistry described herein.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3230265 | PMC |
| http://dx.doi.org/10.1021/ol100845z | DOI Listing |
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Seebach's conjunctive reagent enables double cyclizations.
Org Lett
June 2010
Department of Chemistry, Princeton University, Frick Chemical Laboratory, Princeton, New Jersey 08544, USA.
When ketones flanked on both sides by nucleophilic atoms react with Seebach's nitropropenyl pivaloate reagent, direct couplings take place to give two new ring systems and three bonds. Cis-ring fusions are observed in unions leading to 5,5-, 5,6-, and 6,6-bicycles. Densely functionalized and rigid frameworks may be rapidly formed by the chemistry described herein.
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