Event Information

Seong Du Lee (Duke University)
Gold(I)-Catalyzed Intermolecular Enantioselective Hydroamination of 1-Alkenes with Cyclic Ureas
Abstract:

As a means of achieving enantiomerically enriched nitrogen-containing compounds, the enantioselective hydroamination of alkenes would be an efficient method. However, the lower reactivity of alkenes hindered to accomplish this goal and still remains a challenge task. Herein we report the gold(I)-catalyzed enantioselective intermolecular hydroamination of unactivated 1-alkenes with cyclic ureas. The enantioselective hydroamination of 1-t-Bu-2-imidazolidinone (0.4M) and 1-octene (60 eq.) with [(S)-4]Au2Cl2 [(S)-4 = (S)-3,5-t-Bu-4-MeO-MeOBIPHEP] (2.5 mol %) and AgOTf (5 mol %) in m-xylene at 100 ℃ for 48 h led to isolation of 1-t-Bu-3-(2-octanyl)-2-imidazolidinone in 89 % yield with 78 % ee.

Preliminary Examination Seminar

Monday, March 23, 2009, 2:00pm
Student Exams Seminar