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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 6.

Scope of Electrophiles in Allylic Substitution Reactionsa

graphic file with name nihms536713t64.jpg
Entry Electrophiles Pronueleophlies Products Yieldb (%)
graphic file with name nihms536713t65.jpg graphic file with name nihms536713t66.jpg
1c PG = Boc 2b 1g graphic file with name nihms536713t67.jpg 10a 89
2c PG = Bz 2c 1g 90
3d graphic file with name nihms536713t68.jpg 2d 1g graphic file with name nihms536713t69.jpg 10b 90
4e graphic file with name nihms536713t70.jpg 2e 1g graphic file with name nihms536713t71.jpg 10c 87
(tranc: cis = 10:1)i
graphic file with name nihms536713t72.jpg graphic file with name nihms536713t73.jpg
5f PG = Boc 2b 4a graphic file with name nihms536713t74.jpg 10d 85
6f PG = Bz 2c 4a 20
7f PG = Piv 2f 4a 70
8f, g graphic file with name nihms536713t75.jpg 2d 4a graphic file with name nihms536713t76.jpg 10e 94
9e, h graphic file with name nihms536713t77.jpg 2g graphic file with name nihms536713t78.jpg graphic file with name nihms536713t79.jpg 10f 91
(L:B=2.6:1)i
1b
graphic file with name nihms536713t80.jpg 10f’
10e, h 2h 1b graphic file with name nihms536713t81.jpg 10g 88
(L:B=1.9:1)i
graphic file with name nihms536713t82.jpg
graphic file with name nihms536713t83.jpg 10g’
11e, h graphic file with name nihms536713t84.jpg 2i 1b graphic file with name nihms536713t85.jpg 10h 93
(L:B=1:4.5)i
graphic file with name nihms536713t86.jpg 10h’
a

Reaction conducted on a 0.1 mmol scale at 0.1 M.

b

Isolated yield after chromatographic purification.

c

3 equiv of NaN(SiMe3)2 and 2 equiv of 2.

d

3 equiv of KN(SiMe3)2 and 2 equiv of 2.

e

3 equiv of LiN(SiMe3)2 and 2 equiv of 2.

f

5 equiv of KN(SiMe3)2 and 3 equiv of 2.

g

Reaction conducted at 50 °C.

h

Reaction conducted at 0 °C.

i

Ratio of trans:cis or line-ar:branched (L:B) determined by 1H NMR.