Seebach's conjunctive reagent enables double cyclizations.
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.
Chandler
Brent D
BD
Department of Chemistry, Princeton University, Frick Chemical Laboratory, Princeton, New Jersey 08544, USA.
Roland
Jason T
JT
Li
Yukai
Y
Sorensen
Erik J
EJ
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007202:Indicators and Reagents; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; D007202:Indicators and Reagents; D026121:Indole Alkaloids; D007659:Ketones; C503673:citrinadin A