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. Author manuscript; available in PMC: 2014 Sep 5.
Published in final edited form as: Chem Rev. 2013 Jun 17;113(8):5701–5765. doi: 10.1021/cr4000144

Table 5.

a) Synthesis of Bridged Orthoamides via Schmidt Reaction of 2-Azidoalkyl Ketals by Aubé; b) Conversion of Bridged Orthoamides to Bridged Lactams

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entry 191 n R1 R2 yield of
193 (%)
1 191a 1 t-Bu C6H5 88
2 191b 1 t-Bu 4-MeO-C6H4 92
3 191c 1 t-Bu 4-NO2-C6H4 94
4 191d 1 H C6H5 59
5 191e 1 H SPh 78a
6 191f 0 H C6H5 91
b)
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a

TMSOTf.