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. Author manuscript; available in PMC: 2009 Sep 30.
Published in final edited form as: J Am Chem Soc. 2008 Jun 25;130(29):9244–9245. doi: 10.1021/ja803890t

Table 3.

Diastereoselective Transformations of Propargyl Esters

graphic file with name nihms-110691-t0019.jpg
entry propargyl ester imine azepine yield (dr)a
1 graphic file with name nihms-110691-t0020.jpg 5a graphic file with name nihms-110691-t0021.jpg 99% (> 20:1)
2 graphic file with name nihms-110691-t0022.jpg 11 graphic file with name nihms-110691-t0023.jpg 73% (> 20:1)
3 graphic file with name nihms-110691-t0024.jpg 2b graphic file with name nihms-110691-t0025.jpg 73% (3.3:1)
4 graphic file with name nihms-110691-t0026.jpg 2b 83% (1.4:1)
5 graphic file with name nihms-110691-t0027.jpg 2b graphic file with name nihms-110691-t0028.jpg 58%b (2.5:1)
a

Conditions: 1.3 equiv of propargyl ester, 5% 4, CH2Cl2, rt.

b

Conditions: 2 equiv of propargyl ester, 10% 4, dichloromethane, 60 °C. Ar’ = 4-HO-2,6-Me2-C6H2.