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. Author manuscript; available in PMC: 2015 Sep 8.
Published in final edited form as: Angew Chem Int Ed Engl. 2014 Jul 15;53(37):9904–9908. doi: 10.1002/anie.201405356

Table 1.

Catalyst optimization for the intramolecular Rh(II)-catalyzed dihydroazepine formation[a]

graphic file with name nihms626770u1.jpg
Entry Rh2L4 Temp.(°C) Time Yield 2a(%)[b],[c]
1 Rh2(Ooct)4 140[d] 0.25 h 54 (34)
2 Rh2(OAc)4 140[d] 0.25 h 47 (48)
3 Rh2(tpa)4 140[d] 0.25 h 18 (70)
4 Rh2(OPiv)4 140[d] 0.25 h 58 (18)
5 Rh2(esp)2 140[d] 0.25 h 66 (33)
6 Rh2(Adc)4 140[d] 0.25 h 68 (17)
7 Rh2(Adc)4 60 16 h 74 (14)
[a]

Only one diastereomer of the dihydroazepine product 2a was observed by 1H NMR in all cases.

[b]

Isolated yield.

[c]

NMR yield of imine 3 in parentheses.

[d]

Reaction was performed in a microwave apparatus.