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. Author manuscript; available in PMC: 2008 Dec 5.
Published in final edited form as: Org Lett. 2005 Jun 23;7(13):2571–2573. doi: 10.1021/ol050630b

Table 3.

Effect of Nitrogen Protecting Group and Ester Substituent on Selectivitya

graphic file with name nihms63773t3.jpg

ent nitrogen PG ester R R1 yield, (SM) %a ee, %b
1 Phthalimide t-Butyl 5a Ph 6a 91 88
2 Phthalimide Methyl 5b Ph 6b 35 (35) 10
3 Phthalimide Cyclohexyl 5c Ph 6c 0 -
4 Phthalimide Benzyl 5d Ph 6d 85 20
5 Succinimide t-Butyl 5e Ph 6e 61 71
6 Tosyl t-Butyl 5f Ph 6f 86 81
7 Tosyl t-Butyl 5f 4-BrPh 6g 23 (67) 84
a

Isolated yields. Yields in parenthesis are for recovered starting materials.

b

Chiral HPLC analysis.