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. Author manuscript; available in PMC: 2013 Mar 21.
Published in final edited form as: J Am Chem Soc. 2012 Mar 5;134(11):5131–5137. doi: 10.1021/ja209390d

Table 2.

Optimization of reaction parameters.a

graphic file with name nihms361777u2.jpg
entry R3, R4 pdt solvent additive yield (%)b ee (%)c
1 Bn, CF3 (2a) 7a DCM -- 12 35
2 Me, CF3 (2b) 7b DCM -- 12 42
3 Me, Me (2c) 7c DCM -- 73 78
4 Me, Me (2c) 7c DCM --d 13 --
5 Me, Me (2c) 7c DCM --e 0 --
6 Me, Me (2c) 7c DCM K2CO3 73 78
7 Me, Me (2c) 7c DCM 2,6-lutidine 0 --
8 Me, Me (2c) 7c DCM 4Å MS 86 81
9 Me, Me (2c) 7c DCE 4Å MS 87 79
10 Me, Me (2c) 7c CHCl3 4Å MS 80 72
a

Reactions conducted under inert atmosphere on 0.2 mmol scale for 2 h.

b

Isolated yield.

c

Determined by chiral stationary phase SFC.

d

No (R)-BINOL was employed.

e

No SnCl4was employed.