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. Author manuscript; available in PMC: 2013 Sep 17.
Published in final edited form as: Angew Chem Int Ed Engl. 2012 Aug 24;51(38):9581–9586. doi: 10.1002/anie.201205001

Table 1.

Trapping of tertiary organolithium intermediates derived from nitriles with p-anisaldehyde.a

graphic file with name nihms415543u2.jpg
Entry R Yield [%]
1 tBu 71
2 graphic file with name nihms415543t1.jpg 73
3 graphic file with name nihms415543t2.jpg 66
4 graphic file with name nihms415543t3.jpg 71
5 graphic file with name nihms415543t4.jpg 61
6 graphic file with name nihms415543t5.jpg 59
7 graphic file with name nihms415543t6.jpg 70
a

Conditions: 1.5 equiv nitrile, 3.0 equiv LiDBB, −78 °C, 1 min; 1 equiv aldehyde. LiDBB = lithium di-tert-butylbiphenylide. TIPS = triisopropylsilyl.