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. Author manuscript; available in PMC: 2010 Jun 24.
Published in final edited form as: J Am Chem Soc. 2009 Apr 22;131(15):5372–5373. doi: 10.1021/ja9001162

Table 3.

Enantioselective Intermolecular Hydroamination of 1-Alkenes (60 equiv) with Imidazolidin-2-ones Catalyzed by a Mixture of [(S)-4](AuCl)2 (2.5 mol %) and AgOTf (5 mol %) in m-Xylene at 100 °C for 48 h.

entry nucleophile alkene product yield (%)a ee (%)b
graphic file with name nihms-106298-t0013.jpg graphic file with name nihms-106298-t0014.jpg graphic file with name nihms-106298-t0015.jpg
1 R = Me (1) n = 5 86 76
2 R = Ph n = 5 80 71
3 R = 4-C6H4F n = 5 81 74
4 R = t-Bu n = 5 89 78
5 R = Me (1) n = 7 83 74
6 R = Me (1) n = 9 76 75
graphic file with name nihms-106298-t0016.jpg
a

Yield of isolated, regiochemically pure material of >95% chemical purity.

b

Enantiopurity determined by HPLC analysis employing chiral stationary phase.