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. Author manuscript; available in PMC: 2010 Oct 1.
Published in final edited form as: Org Lett. 2009 Oct 1;11(19):4362–4365. doi: 10.1021/ol901692n

Table 1.

Enantioselective Propargylations with Methanesulfonamide

graphic file with name nihms-142838-t0006.jpg

entry aldehyde yield (%)a drb product
1 graphic file with name nihms-142838-t0007.jpg 81 >20:1 3a
2 graphic file with name nihms-142838-t0008.jpg 77 >20:1 3b
3 graphic file with name nihms-142838-t0009.jpg 81 10:1 3c
4 graphic file with name nihms-142838-t0010.jpg 69 5:1 3d
5 graphic file with name nihms-142838-t0011.jpg 64 7:1 3e
6 graphic file with name nihms-142838-t0012.jpg 65 9:1 3f
7 graphic file with name nihms-142838-t0013.jpg 82c >20:1 3g
8 graphic file with name nihms-142838-t0014.jpg 82c >20:1 3h
a

Isolated yields after purification over silica gel.

b

Diastereomeric ratios determined by 1H NMR analysis on crude material.

c

Reaction run at −45 °C in MeCN.