226546-04-9Relevant academic research and scientific papers
An asymmetric route to novel chiral cyclohexenones with spiro-connected cyclopentenes. Further utility of chiral bicyclic thiolactams and the [3,3] thio-Claisen products
Lemieux,Devine,Mechelke,Meyers
, p. 3585 - 3591 (2007/10/03)
Sequential allylation of chiral, nonracemic thiolactam 8 affords clean thio-Claisen [3,3] products 11. The stereoselectivity of the rearrangement was found to be on the order of 10-11:1, with the exo-endo products responsible for the mixture. Addition of hydride or methyllithium-cerium chloride gave clean addition to the thiolactam in the form of its iminium salts 12. Hydrolysis gave 4,4-dialkylcyclohexenones 15, which were cyclized to the cyclopentene derivatives 16 using Grubbs' catalyst.
