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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 4.

Scope of Diphenylmethane Derivatives in Allylic Substitution Reactionsa

graphic file with name nihms536713t30.jpg
Entry Pronucleophlles Products Yieldb(%)
1 graphic file with name nihms536713t31.jpg 4a graphic file with name nihms536713t32.jpg 5aa 95
2 graphic file with name nihms536713t33.jpg 4b graphic file with name nihms536713t34.jpg 5ba 84
3 graphic file with name nihms536713t35.jpg 4c graphic file with name nihms536713t36.jpg 5ca 95
4 graphic file with name nihms536713t37.jpg 4d graphic file with name nihms536713t38.jpg 5da 73
5c graphic file with name nihms536713t39.jpg 4e graphic file with name nihms536713t40.jpg 5ea 87
6d graphic file with name nihms536713t41.jpg 4f graphic file with name nihms536713t42.jpg 5fa 90
7e, g graphic file with name nihms536713t43.jpg 4g graphic file with name nihms536713t44.jpg 5ga 68
8f, g graphic file with name nihms536713t45.jpg 4h graphic file with name nihms536713t46.jpg 5ha 70
a

Reaction conducted on a 0.1 mmol scale with 1 equiv of 4 and 3 equiv of 2a at 0.1 M.

b

Isolated yield after chromatographic purification.

c

1.5 equiv of LiN(SiMe3)2 and 1.1 equiv of 2a.

d

1.5 equiv of KN(SiMe3)2 and 2 equiv of 2a.

e

8 equiv of KN(SiMe3)2.

f

10 equiv of KN(SiMe3)2.

g

Reaction conducted at 50 °C.