83845-56-1Relevant 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.
Photochemistry of (o-Methylphenyl)alkadienes: Attempted Intramolecular Trapping of the Resulting o-Xylylenes
Hornback, Joseph M.,Barrows, Russell D.
, p. 90 - 98 (2007/10/02)
The photochemistry of a series of o-methylphenyl dienes was investigated in order to determine if the resulting o-xylylenes could be trapped in an intramolecular Diels Alder reaction in synthetically useful yields.Irradiation of 3 gave meta-isomer 4 as the major product along with lower yields of double bond migration product 5 and the desired cycloadduct 6.The best yield of 6 (24percent) was obtained by irradiation of 3 with a low-pressure mercury vapor lamp at low temperatures.The other compounds investigated gave none of the intramolecular Diels-Alder product of the o-xylylene.Irradiation of 17 gave only double bond migration product 18.Irradiation of 22 gave an excellent yield of (2+2) cycloadduct 23.Irradiation of 26 gave meta-isomer 28, double bond migration product 27, and 29, a (2+2) cycloadduct of 28.
