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Please login to access the full content or check if you have access via4.4.40.24 Method 24: Formation of 2-Substituted Allylsilanes by Silylcupration of Allene
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Sarkar, T. K., Science of Synthesis, (2002) 4, 866.
2-Substituted allylsilanes have been prepared by silylcupration of allene by (dimethylphenylsilyl)copper(I) reagent 88, followed by conjugate addition of the resultant allylsilane/vinylcopper intermediate 89 with α-enones in the presence of boron trifluoride–diethyl ether complex as additive; this method has been used for the preparation of, for example, allylsilanes 90 and 91 (Scheme 42).[157] Use of the boron trifluoride–diethyl ether complex is not mandatory here, but its presence significantly increases the yields of the products.[157,158] Besides 1,4-addition, the allylsilane/vinylcopper intermediate 89 also takes part in a number of other reactions, including alkylation and acetylation, to give a range of allylsilanes.[158]
Meeeee 88 8-Meeeeeeeeee Meeeeeeeeeee ee Meeeeeeeeeeeee ee Meeeee[888]
Meeeeeeeeeee eee eeee eeeeeeeee ee eeeeeeeeeeeeee ee eeeeeee eeee eeeeeee eee(eeeeeeeeeeeeeeeeeee)eeeeeee; eeeeeee, eee eeeee ee eeee eeeeee ee eeeeeee.[888,888]
Meeeeeeeeeee Meeeeeeee
8-[(Meeeeeeeeeeeeeeeeee)eeeeee]-8-eeeeeeeee-8-ee-8-eee (88); Meeeeee Meeeeeeee:[888,888]
M eeee ee Me8MeMeMe (8 eeee), eeeeeeee ee MMM (8 eM), eee eeeee ee eeeeeee ee e eeeeeee eeeeeeeeee ee MeMM (888 ee, 8 eeee) ee MMM (8 eM) ee 8°M. Mee eeeee eeeeeee eee eeeeeee ee eeee eeeeeeeeeee eee ee eeeeeeeeee 88 eee, eee eee eeeeeeeee eeee ee (eeeeeeeeeeeeeeeeeee)eeeeee(M) eeeeeee 88 (8 eeee) ee MMM (8 eM) eee eeeeee ee −88°M eee e eeeeee eeeeee ee eeeeee eee eeeee eeee e eeeeeee. Meeee 8 e ee eeeeeeee ee eeee eeeeeeeeeee, eee eeeeeee eee eeeeee ee −88°M, MM8•MMe8 (8.88 eM, 8 eeee) eee eeeee, eee eee eeeeeee eee eeeeeee eee eeeeeee 88 eee. Mee eeeeeeeee eeeeeee eee eeeeee ee −88°M eee eeee (M)-8-eeeeeeeee-8-ee-8-eee (888 ee, 8.8 eeee) ee MMM (8 eM) eee eeeee eeeeeeee ee −88°M; eee eeeeeeeee eeee eee eeee ee eeee eeeeeeeeeee eee 8 e. Meeee eeeeee eeeeeee ee 8°M (eeee 8.8 e), eee eeeeeee eee eeeeeeee eeee eee. ee MM8Me eee eeeeeeeee eeeee eeee Me8M. Mee eeeeeee eeeee eee eeeee (MeMM8) eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee ee e eeeeee eeeeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:88) ee eeee e eeeeeeeee eee; eeeee: 888 ee (88%).
References
[157] | Meeeeee, M.; Meeeíe, M.; Meeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[158] | Meeeee, M. M.; Meeeeeee, M.; Meeeáeee, M. M.; Meeeee, M. M.; Meeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[159] | Meeeeee, M.; Meeeee, M.; Meeeeeee, M.; Meeeáeee-Meeee, M. M.; Meeeee, M. M., Meeeeeeeeee, (8888) 88, 888. |
[160] | Meeeeee, M.; Meeeee, M. M., M. Meee. Mee., Meee. Meeeee., (8888), 8888. |
[161] | Meeeee, M. M., eeeeeeee eeeeeeeeeeeee. |