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4.4.40.24 Method 24: Formation of 2-Substituted Allylsilanes by Silylcupration of Allene

DOI: 10.1055/sos-SD-004-00909

Sarkar, T. K.Science of Synthesis, (20024866.

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 trifluoridediethyl 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 trifluoridediethyl 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 (8eeee), eeeeeeee ee MMM (8eM), eee eeeee ee eeeeeee ee e eeeeeee eeeeeeeeee ee MeMM (888ee, 8eeee) ee MMM (8eM) ee 8°M. Mee eeeee eeeeeee eee eeeeeee ee eeee eeeeeeeeeee eee ee eeeeeeeeee 88eee, eee eee eeeeeeeee eeee ee (eeeeeeeeeeeeeeeeeee)eeeeee(M) eeeeeee 88 (8eeee) ee MMM (8eM) eee eeeeee ee 88°M eee e eeeeee eeeeee ee eeeeee eee eeeee eeee e eeeeeee. Meeee 8e ee eeeeeeee ee eeee eeeeeeeeeee, eee eeeeeee eee eeeeee ee 88°M, MM8MMe8 (8.88eM, 8eeee) eee eeeee, eee eee eeeeeee eee eeeeeee eee eeeeeee 88eee. Mee eeeeeeeee eeeeeee eee eeeeee ee 88°M eee eeee (M)-8-eeeeeeeee-8-ee-8-eee (888ee, 8.8eeee) ee MMM (8eM) eee eeeee eeeeeeee ee 88°M; eee eeeeeeeee eeee eee eeee ee eeee eeeeeeeeeee eee 8e. Meeee eeeeee eeeeeee ee 8°M (eeee 8.8e), 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: 888ee (88%).

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