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. Author manuscript; available in PMC: 2014 Nov 20.
Published in final edited form as: J Am Chem Soc. 2013 Nov 12;135(46):17602–17609. doi: 10.1021/ja409511n

Table 1.

Preliminary Results of Allylic Substitution Reactionsa

graphic file with name nihms536713t1.jpg
Entry Pronuelephiles Base Product Yieldb (%)
1d graphic file with name nihms536713t2.jpg 1a LiN(SiMe3)2 graphic file with name nihms536713t3.jpg 3aa 80
2d graphic file with name nihms536713t4.jpg 1a NaN(SiMe3)2 graphic file with name nihms536713t5.jpg 3aa (99c)
3 graphic file with name nihms536713t6.jpg 1a NaN(SiMe3)2 graphic file with name nihms536713t7.jpg 3aa (99c)
4 graphic file with name nihms536713t8.jpg 1c NaN(SiMe3)2 graphic file with name nihms536713t9.jpg 3ca 27
5 graphic file with name nihms536713t10.jpg 1c KN(SiMe3)2 graphic file with name nihms536713t11.jpg 3ca 70
6 graphic file with name nihms536713t12.jpg 4a KN(SiMe3)2 graphic file with name nihms536713t13.jpg 5aa 10
a

Reaction conducted on a 0.1 mmol scale with 1 equiv of pronucleophile and 2 equiv of 2a at 0.1 M.

b

Yield determined by 1H NMR spectroscopy of the crude reaction mixture.

c

Isolated yield after chromatographic purification.

d

1 equiv of NEt3.