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. Author manuscript; available in PMC: 2016 Feb 16.
Published in final edited form as: Angew Chem Int Ed Engl. 2015 Jan 7;54(8):2410–2415. doi: 10.1002/anie.201411493

Table 1.

Solvent and substituent control stereoinduction.

graphic file with name nihms699227u1.jpg
Entry Y Solvent Temperature Additive 13-(S) : 13-(R)
1 NOH DMF 22 °C – 1.5 : 1.0
2 NOH CH2Cl2 22 °C – 1.5 : 1.0
3 NOH EtOH 22 °C – 3.8 : 1.0
4 NOH EtOH −20 °C – 3.0 : 1.0
5 NOH 1:9 MeOH/CH2Cl2 22 °C NH4OH (1%) 2.1 : 1.0
6 NOH EtOH 22 °C AcOH (1 equiv.) 2.7 : 1.0
7 NOH TFE 22 °C – 2.3 : 1.0
8 NOH 1:1 EtOH/H2O 22 °C – 4.7 : 1.0
9 NOH 1:3 EtOH/H2O 22 °C – 7.9 : 1.0
10 O 1:4 EtOH/H2O 22 °C – 1.2 : 1.0
11 CH2 1:4 EtOH/H2O 22 °C – 1.1 : 1.0