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. Author manuscript; available in PMC: 2010 Jun 21.
Published in final edited form as: J Am Chem Soc. 2008 Dec 10;130(49):16502–16503. doi: 10.1021/ja807696e

Table 1.

Redox isomerisation of tethered (tosylamino)propargyl alcohols

graphic file with name nihms-86569-t0006.jpg
Entry n R Yielda
1 1 H (6a) 75%
2 1 Me (6b) 79%
3 1 -(CH2)2Ph (6c) 92%
4 1 -(CH2)4CO2Et (6d) 77%
5b 2 H (6e) 77%
6b 2 Me (6f) 72%
7b 2 -(CH2)2(6g) 68%
8b 2 -CH2OBn (6h) 80%
a

All yields are for pure, isolated products.

b

Performed with 10 mol% CSA (see Scheme 1).