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. 2008 Jun 24;130(29):9182–9183. doi: 10.1021/ja800402g

Table 1. Reaction of 5a with 1 or 2 Activated in situa.

entry borane source activator time (h) conversionb (%) 9a:10ab
1 1 I2 10 40 4.3:1
2 1 I2 19 >90 4.7:1
3 2 I2 5 >90 7:1c
4 2 I2 5 >90 18:1d
5 1 TfOH 5 >90 >20:1
a

A 0.1 M solution of 5 and 2 equiv of 1 or 2 at −78 °C in CH2Cl2 was treated with 2 equiv of activator, warmed to −20 °C, stirred (time), and quenched with NaOOH/MeOH·H2O.

b

NMR assay.

c

Activated at −20 °C and warmed to −10 °C.

d

Warmed to −10 °C.