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. Author manuscript; available in PMC: 2015 Aug 18.
Published in final edited form as: Org Lett. 2015 Jan 12;17(3):572–575. doi: 10.1021/ol503591d

Table 2.

Effect of the Chiral Auxiliary on Selectivitya

entry enamides products time [h] yield [%]b[dr]c
1 graphic file with name nihms716014t1.jpg
3b
graphic file with name nihms716014t2.jpg
4b
14 58 [93:7]
2 graphic file with name nihms716014t3.jpg
3c
graphic file with name nihms716014t4.jpg
4c
12 51 [91:9]
3 graphic file with name nihms716014t5.jpg
3d
graphic file with name nihms716014t6.jpg
4d
12 72 [>95:5]
4 graphic file with name nihms716014t7.jpg
ent-3d
graphic file with name nihms716014t8.jpg
ent-4d
12 63 [>95:5]
a

Reaction condition: 1.1 equiv NFSI, 2 % H2O in CH3CN, 40 °C; and then, DMP, NaHCO3, CH2Cl2, rt.

b

Isolated yields.

c

Diastereomeric ratios [dr] were determined by 1H or/and 19F NMR spectroscopy.