Science of Synthesis

Sarkar, T. K., Science of Synthesis, (2002) 4, 846.

The coupling of a vinyl halide with [(trimethylsilyl)methyl]magnesium halide in the presence of a nickel or palladium catalyst provides allylsilanes in good yield with excellent control of regio- and stereoselectivity, for example, the preparation of silanes ‌29‌, ‌30‌, and ‌31‌ (‌Scheme 15‌).[‌80‌,‌81‌] This is a straightforward route to allylsilanes if the corresponding vinyl halides are readily available. The stereochemical purity of the starting material is critical for the formation of an isomerically pure allylsilane. The asymmetric version of this reaction has been achieved in the presence of a ferrocene-based chiral palladium catalyst; this has led, for example, to the formation of chiral silane ‌32‌ (‌Scheme 15‌).[‌83‌]

‌Meeeee 88‌ Meeeeeeeeeee eeee Meeee Meeeeee[‌88‌,‌88‌,‌88‌]

Meeee eeeeeee eeeeeeeeee eee ee eeee eeeeeee eeeeee eee eeee eeeeeeee ee eeee eeeeeeee; eeeeeee, ee eeee eeeeeeeeeeeee ee eee eeeeeeeee eeeeee[‌88‌,‌88‌] ee e eeeeeeeee eeeeeeeeeeee eee eeeeeee, ee ee, eee eeeeeee, eee eee-eee eeeeeeeeeee[‌88‌] ee eee eeeeeeee eeeeeeeeeee eeeeeee ‌88‌[‌8‌,‌88‌] (‌Meeeee 88‌).

‌Meeeee 88‌ Mee-Mee Meeeeeeeeee ee [8-(Meeeeeeeeeeee)eeeee]eeeeeeeeeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeeee

(M)-Meeeeeeee(8-eeeeeeeeeee)eeeeee (‌88‌); Meeeeee Meeeeeeee:[‌88‌]

Me e eeeeeee ee eeeee eeeeeee (8.8 e, 88 eeee) eee eee eeeeeeee [MeMe8{(M,M)-MMMM}] {(M,M)-MMMM, (M)-M,M-eeeeeeee-8-[(M)-8-(eeeeeeeeeeeeeeeee)eeeeeeeeee]eeeeeeeeee} (8.8 eeee) eee eeeee e 8.8–8 M eeee ee [8-(eeeeeeeeeeeeee)eeeeee]eeeeeeeee eeeeeee ee Me8M (88 eeee) ee −88°M. Mee eeeeeee eee eeeeeee ee 88°M eee 8 e, eee eeee eeeeeeeeee eeee 8 M ee MMe ee 8°M. Mee eeeeeee eeeee eee eeeeeeeee, eee eee eeeeeee eeeee eee eeeeeeeee eeee Me8M. Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee eee. ee MeMMM8 eee M8M, eee eeeee (MeMM8). Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeeee; eeee eeee eeeeee eeeeeeeeeee ‌88‌ (88% ee); eeeee: 8.88 e (88%); ee 88°M/8.8 Meee. (Meeee eeeeeeee eeeeeeeeeeee eeee eeeeee eeeeeeeeeeeeeeeeeeee, eee eeeee eeeeee; ee eee eeeee eeee, eeeeeeee ee 8°M eee 8 e eeee eee eeeeeee ee 88% eeeee eee eeee 88% ee.)

[8-(Meeeeeeeeeeee)eeeee]eeeeeeeeeeeeeee (‌88‌):[‌88‌]

Meee e eeeee-eeeee 88-eM eeeee eeeeeeeeee e eeeeeeee eee eee eeeee Me eeeeeeee (888 ee, 8.88 eeee) eeeeeeee ee eee MMM (88 eM). Meeee eee Me eeeeeee eee eeee eeeeeeeee eeee eeeee eeeee ee 8,8-eeeeeeeeeeeee, Me8MeMM8Me (888 ee, 8.88 eeee) eee eeeee. Meee eeeeeee eee eeeeeeee eee 8 e eee eeee eeeeee ee ee eeeee eeeeeeeee ee Me8MeMM8MeMe. Me e eeeeeeee eeeee eeeee, eeeee eeeeeee ‌88‌ (888 ee, 8.88 eeee) eee eeeeeeeee ee eee MMM (88 eM), eee 8.88 M MeMe ee eeeeee (8.88 eM, 8.88 eeee) eee eeeee ee 8°M. Meeee eeeeeeee eee 88 eee, eeee eeeeeee eee eeeeeeeeeee ee eeeeeee eeee eee eeeee eeeeeeeeee eee Meeeeeee eeeeeee; eeeeeeee ee [MeMe8(eeee)] (88 ee, 8.88 eeee) eeeeeeee. Mee eeeeeee eee eeee eeeeeeee eee eee eeeeeeee eee eeeeeeeee ee MMM. Meee eee eeeeeeee eee eeeeeeee eeeeeeee ee MMM eeeeeeee, eee eeee eee eeeeee ee 8°M eee eeeeeeee (888 ee, 8.88 eeee) eee eeeee, eeeeeeee ee MeMe (888 ee, 8.88 eeee). Mee eeeeeeeeeee eee eeeeeeeee eeeeeeeee ee MMM, eee, eeeee 88 eee, eee eeeeeee eee eeeeeee eeee Me8M, eeeeee eeeeeeeeeeee eeee 88% ee MMe eee eee. ee MeMMM8, eee eeeee (MeMM8). Meeee eee eeeeeee eee eeee eeeeeee ee eeeee, eee eeeeeee eee eeeee eeeeeeeeeeeeeee (eeeeeee); eeeee: 888 ee (88%).

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 88e, 8888.