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. Author manuscript; available in PMC: 2017 Aug 1.
Published in final edited form as: J Pept Sci. 2014 Dec 11;21(1):53–59. doi: 10.1002/psc.2723

Table 1.

graphic file with name nihms688902u1.jpg
Entry Reducing Conditions Sec Intermediate Electrophile Notes
1 LiBEt3H (ref. 17) graphic file with name nihms688902t1.jpg graphic file with name nihms688902t2.jpg Trace product formed. Selenol intermediate readily re-formed 1 under the basic reaction conditions.
2 In(I)I (refs. 21 & 22) graphic file with name nihms688902t3.jpg graphic file with name nihms688902t2.jpg No product formed. In(III)I diorganyl selenoate unreactive to the tertiary alkyl chloride electrophile.
3a Zn/HCl (refs. 15 & 16) graphic file with name nihms688902t4.jpg graphic file with name nihms688902t5.jpg 84% Fmoc-Sec(Xan)-OH product isolated.
3b Zn/HCl (refs. 15 & 16) graphic file with name nihms688902t4.jpg graphic file with name nihms688902t2.jpg 87% Fmoc-Sec(Trt)-OH product isolated.