72525-47-4Relevant academic research and scientific papers
Diastereoselective C?H Bond Amination for Disubstituted Pyrrolidines
Iovan, Diana A.,Wilding, Matthew J. T.,Baek, Yunjung,Hennessy, Elisabeth T.,Betley, Theodore A.
supporting information, p. 15599 - 15602 (2017/11/16)
We report herein the improved diastereoselective synthesis of 2,5-disubstituted pyrrolidines from aliphatic azides. Experimental and theoretical studies of the C?H amination reaction mediated by the iron dipyrrinato complex (AdL)FeCl(OEt2) provided a model for diastereoinduction and allowed for systematic variation of the catalyst to enhance selectivity. Among the iron alkoxide and aryloxide catalysts evaluated, the iron phenoxide complex exhibited superior performance towards the generation of syn 2,5-disubstituted pyrrolidines with high diastereoselectivity.
Metalation of o-Halostyrene Oxides. Preparation of Benzocyclobutenols
Akguen, Eyup,Glinski, Margaret B.,Dhawan, Kasturi L.,Durst, Tony
, p. 2730 - 2734 (2007/10/02)
o-Bromo- and o-iodostyrene oxides are converted in fair to good yield to benzocyclobutenols upon treatment with n-BuLi and MgBr2 in THF or ether at -78 deg C, followed by warming to room temperature.The reaction involves initial halogen-lithium exchange followed either by MgBr2-initiated opening of the epoxide function to a haloalkoxide or rearrangement of the epoxide function to a ketone or aldehyde followed by cyclization.Benzocyclobutenol formation was not successful in the case of o-halostilbene oxides.
