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. Author manuscript; available in PMC: 2012 Aug 17.
Published in final edited form as: J Am Chem Soc. 2011 Jul 25;133(32):12466–12469. doi: 10.1021/ja205714g

Table 4.

Exploration of Various Enalsa

graphic file with name nihms314274u3.jpg
entry R3 product yield (%) dr ee (%)
1b graphic file with name nihms314274t3.jpg 2b 3n 62 11/1 66
2c 4-NO2-C6H4 2c 3o 99 14/1 93
3d 4-Br-C6H4 2d 3p 58 17/1 91
4d Ph 2e 3q 48 20/1 90
a

Conditions: aldehyde 2, 0.2 mmol; 1a, 0.1 mmol; A2, 20 mol%; C4; 20 mol%; solv., 0.8 mL; all reactions were carried out under Ar in the presence of 4A MS at 0 °C. The trans/cis ratio is determined by 1H NMR prior to purification. The ee’s are determined by chiral HPLC.

b

15 h in acrylonitrile.

c

36 h in CH2Cl2.

d

66 h in CH2Cl2.