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. Author manuscript; available in PMC: 2016 May 20.
Published in final edited form as: Angew Chem Int Ed Engl. 2015 Jun 25;54(33):9517–9522. doi: 10.1002/anie.201502341

Table 2.

Reaction optimization for aliphatic substrates.[a]

graphic file with name nihms785914t2.jpg

Entry Substrate Temp [°C] Product Yield [%][b] e.r.[d]
1 E-1c-Br −30 a-2c-OMe-Br 92[c] 81:19
2 E-1c-NO2 −30 a-2c-OMe-NO2 86 87:13
3 Z-1c-NO2 −30 s-2c-OMe-NO2 87 99.5:0.5
4 Z-1c-NO2 24 s-2c-OMe-NO2 75 97:3
5[e] Z-1c-NO2 −30 s-2c-OMe-NO2 79 97:3
[a]

The r.r. (defined as ratio of 2:5, see Table 4) was more than 20:1 and d.r. was more than 99:1 in all instances.

[b]

Determined by NMR using MTBE as added external standard.

[c]

5% of cyclized product was also seen by NMR.

[d]

Determined by chiral-phase HPLC.

[e]

2 mol% catalyst was used.