Science of Synthesis

Frost, C. G.; Le Nôtre, J., Science of Synthesis, (2008) 36, 326.

The addition of allylsilanes and allylstannanes to aldehydes has been extensively studied as a mild and efficient method for the synthesis of alcohols.[‌346‌] The reactions are promoted by Lewis acids, Lewis bases, or additionally by fluoride ion in the case of allylsilanes. Interestingly, the Lewis acid promoted addition of but-2-enylsilanes provides predominantly syn-homoallyl alcohol ‌118A‌ no matter what the geometry of the double bond in the starting material (‌Scheme 66‌).[‌351‌] Similarly, the Lewis acid induced syn addition of allylstannanes to alkyl aldehydes is independent of initial allyl geometry.[‌352‌]

‌Meeeee 88‌ Mee Meeeeeee ee Mee-8-eeeeeeeeeee ee ee Meeeeeee[‌888‌]

Me eee eeee ee eee Meeee eeee eeeeeeee eeeeeeee ee eeeeeeeeeeeeeeee ee α-eeeeeee eeeeeeee eeeeeeeeeee, eee eeeeeeeeeeeeeeeee eee ee eeeeeeeeee ee eeeeeeeee eeeeeeeee ee Meeee eeee eee eeeeeee-eeeeeeeeee eeeee.[‌888‌–‌888‌] Mee eee-eeeeeee ‌888M‌ eee ee eeeeeeee eeee >888:8 eeeeeeeeeeeeeeeee eeeee eee eeeeeeeee eeeeeeeee eee eeeeeeeee eeeeeee ee eee Meeee eeee (‌Meeeee 88‌). Meeeeeeeeeeee, eeee-eeeeeee ‌888M‌ ee eeeeeeee ee eee eeeee eeeeeee eeeee eee eeeeeeeeee eeeeeeeee eeee-eeeeeeeeeeeeeeeeeee-eeeeeeeee eeeeeeeee eeee 8 eeeeeeeeeee ee eeeee eeeeeeeeeee–eeeeeee eeeee eeeeeee.

‌Meeeee 88‌ Mee Meeeeeeeeeeeeee Meeeeeee ee Meeeeeeeeeeeeeee ee α-Meeeeee Meeeeeee Meeeeeeeeee[‌888‌–‌888‌]

Mee eeeeeeeee ee eeeeeeeeeeeeeeee eeeeeeee eeeeeee eeeeeeee ee eee eeeeeeee ee eeeeeeeeeeee eee eeeeeeeeeeeee eeeeeeeee ee eeeeee Meeee eeeee eee eeee eeeeeeeeeee eeeeeeee.[‌888‌] Meeeeeeeeeee, eee eeeeeeeeeeee ee eeeeeeeee eee eeeeee eeeeeeeeeeeeeeee Meeee eeee eeeeeeeee eeee eeeeeee eeeeeeeeeeeeeee eeeeeeee eeeeeeee ee eeeeeee eeeeeeee eeee eeeeeeeeeee eeeeeeeeeeeeeeeee.[‌888‌–‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeeeeee Meeeeeee, e.e. ‌888‌; Meeeeee Meeeeeeee:[‌888‌]

MeMe8 (8.8 eeeee) eee eeeee ee −88°M ee e eeeeeee ee ee eeeeeeeeeee (8.8 eeeee) eee ee eeeeeeee (8.8 eeeee) ee MM8Me8. Mee eeeeeee eee eeeeeee ee −88°M eee 8 e eee eeee eeeeeeee eeee M8M. Mee eeeeeeee eeee eeeeeeee ee eeeeeeeeeee MMM (eeeeee eee, MMMe8).

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 88e, 8888.
• 8.Meeeee-Meee, (8888) M 88e, 8888.