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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 1.

Orienting studies for the enantioselective intermolecular chloroetherification of E-1b-(Br/OMe/NO2).

graphic file with name nihms785914t1.jpg
Entry Substrate Solvent Conc. [M] Temp. [°C] Yield [%][a] ratio
2b:3b[b] 		d.r.
(a-2b:s-2b)[b] 		e.r.
(2b)[c] 		e.r.
(3b)[c]
1 E-1b-Br MeOH 0.03 24 93 1.8:1 6.8:1 67:33 96:4
2 E-1b-Br MeOH 0.03 −30 94 1.8:1 6.8:1 73:27 98:2
3 E-1b-Br MeOH 0.01 −30 76 1.8:1 5.7:1 71:29 98:2
4[d] E-1b-Br MeOH/MeCN 0.01 −30 76 1.3:1 5.8:1 85:15 99:1
5[d] E-1b-OMe MeOH/MeCN 0.01 −30 86 1.3:1 5.0:1 83:17 97:3
6[d] E-1b-NO2 MeOH/MeCN 0.01 −30 85 1.1:1 3.4:1 92:8 96:4
[a]

Combined yield of a-2b, s-2b, and 3b as determined by NMR analysis with MTBE as added external standard.

[b]

Determined by NMR spectroscopy.

[c]

Determined by chiral-phase HPLC.

[d]

MeOH/MeCN ratio was 3:7.