Sequenced reactions with samarium(II) iodide. Sequential intramolecular Reformatsky/nucleophilic acyl substitution reactions for the synthesis of medium-sized carbocycles.
Samarium(II) iodide was used to access eight- and nine-membered carbocycles via a domino reaction comprised of a Reformatsky reaction followed by a nucleophilic acyl substitution reaction. This method represents a general and efficient approach to a variety of highly functionalized, stereodefined carbocycles.
Molander
Gary A
GA
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
Brown
Giles A
GA
Storch de Gracia
Isabel
I
D000473:Alkanes / Q000737:chemistry*; D000478:Alkylation; D002384:Catalysis; D003500:Cyclization; D007454:Iodides / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D012493:Samarium / Q000737:chemistry*
D000473:Alkanes; D007454:Iodides; D007659:Ketones; D012493:Samarium; C409809:samarium diiodide