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47.1.1.4.4 Method 4: Synthesis by Methylenation with gem-Dimetallic Reagents

DOI: 10.1055/sos-SD-047-00100

Petasis, N. A.Science of Synthesis, (201047204.

Several types of reaction involving gem-dimetallic (1,1-dimetallic) reagents are known.[‌142‌] The methylenation of carbonyl compounds to produce alkenes is possible by a number of methods involving these reagents, particularly those containing combinations of zinc, titanium, or magnesium halides (Scheme 26). gem-Dimetallic reagents are typically able to methylenate aldehydes, ketones, and, in some cases, esters and lactones.

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Mee eeeeeee eee-eeeeeeeeee eeeeeeeeeeeee eeee eee eeeeeeeeeeeee eee eeeee eeeeeeeee ee eeee eeee eeeeeeeeeeeeee eee eeeeeeeee eeeeee. (Meeee 88).[‌888‌‌888‌] Mee eeeeeee, eee Meeeee eeeeeee 888[‌888‌] ee eeeeeeee ee eee eee ee e eeeeeeee eeeeee eee ee eeeeeeee ee eeeeeeeeeee eeee e Meeee eeee ee eeeeeee eeeeeeeeee (Meeee 88, eeeeeee 88).[‌888‌,‌888‌] Mee eee ee eeeeeeeeeeeeee eeee eeee eee eeeeeeee(MM) eeeeeeee ee eeeeeeeeeeeeeee ee e eeeeee eeeeeeeee eee eee eeeeeeeeeeeee ee eeeeeeeee eee eeeeeee (eeeee 8).[‌888‌,‌888‌] Me eeeeeeee eeeeeeeee eeeeeeeee e eeeeee eeeeeee eeeeeeee eeee eee eee eeeee-eeeeeeeee eeeeee (eee Meeeeeee eeeeeee) ee eeee eeeeeeeee (eeeee 8).[‌888‌] Mee eee ee eeee(MM) eeeeeeee ee e eeeeeeee eee eeee eeeeeee eee eeeeee ee eeee eeeeeeee, eee, ee eeeeeeeeeee eeee M,M,M,M-eeeeeeeeeeeeeeeeeeeeeeeeee (eee MeeeeMeeeeee eeeeeee), ee eeeeeeee eee eee eeeeeeeeeeeee ee eeeeee (eeeee 8).[‌888‌,‌888‌]

Meeee 88 Meeeeeee eee Meeeeeeeee eee eee Meeeeeeeeeeee ee Meeeeeee Meeeeeeee eeee eee-Meeeeeeeee Meeeeee[‌888‌‌888‌]

Meeee eee-Meeeeeeeee Meeeeee Meeeeeee eee Meeeeeeeee Mee
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8 Me(MM8MeMe)8MMM Me(MM8MeMe)8MMM (888), β-MeMe8, MMM [‌888‌]
8 Me(MM8MeMe)8MMM Me(MM8MeMe)8MMM (888), MM8MMe8, MMM [‌888‌]
8 MeMeMM8MeMee MM8Me8, Me, MeMe8, MMM [‌888‌,‌888‌]
8 MeMeMM8MeMee MM8Me8, Me, MeMe8, MMM, 88 ee 8°M, 8e [‌888‌,‌888‌]
8 MeMeMM8MeMeeMMMMM MM8Me8, Me, MeMe8 (eee.), MeMe8, MMMMM, MMM, 88°M [‌888‌,‌888‌,‌888‌]
8 MMeMM8MeMee MM8M8, Me, Me8Me, MMM, eeeeee [‌888‌,‌888‌,‌888‌]
8 MMeMM8Me(MeMe)e MM8M8, Me, Me(MeMe)8, MMM [‌888‌]
8 MMeMM8MeMee MM8M8, Me, MeMe8, MMM [‌888‌,‌888‌,‌888‌]
88 MM8(MeM)8 MM8M8, Me, eeeeeeeeee, MMM [‌888‌]
88 MM8(MeM)8 MM8M8, Me, MeMe8 (eee.), MMM [‌888‌,‌888‌‌888‌]
88 MM8(MeM)8 MM8(MeM)8, β-MeMe8, MMM [‌888‌,‌888‌]
88 MMeMM8Me(Me)8Me MM8M8, Me, MMM, 88°M, eeee Me(Me)8Me8 (88) [‌888‌]
88 MeMeMM8Me(Me)8Me MM8Me8, Me, Me(Me)8Me8, MMM, ee [‌888‌]
88 MM8(MeM)8 MM8M8, Me, Me8M [‌888‌]
88 MM8Me8, Me/Me, Me8M, eeee Me(Me)8Me8 (88) [‌888‌]
88 MM8Me8, Me, MeMe8, MMM [‌888‌,‌888‌]

Mee eee-eeeeeeeeee eeeeeee eeeeeeee eeee eeeeeeeeeeeee eee eeeeeeeee eeee [eeeeeeee 888 (M=M); eee Meeeee 88] eee ee eeee eee eee eeeeeeeeeeeee ee eeeeeeee eeeeeeeee eeeee e eeeeeee ee eeeeeeeeee, eeeeeeeee eeee eeee eee eee ee eeeeeeeee eeee ee eeeeeeeeeeeeeeeee (Meeee 88, eeeee 8)[‌888‌,‌888‌] eee eeeeeeee(MM) eeeeeeeeeeee (eeeee 8).[‌888‌] Mee eeeeeeeeeee ee eeeeeeeeeeeee, eeee, eee eeeeeeee(MM) eeeeeeee (eee MeeeeMeeeee eeeeeee) ee eeeeee eee eee eeeeeeeeeeeee ee eeeeeeeee eee eeeeeee (eeeee 8).[‌888‌,‌888‌,‌888‌] Mee eee-eeeeeeeeee eeeeeee eeeeeeee eeee eeeeeeeeeeeee/eeee ee eeee eeeeeeeee eee eee eeeeee eeeeeeeeeeeee ee eeeeeee eeeeeeee eeeeeeeee eeeee eeeeeeeeee eeee eeeeeeeeee eee eeeeeeeee (eeeeeee 88,[‌888‌] 88,[‌888‌‌888‌] eee 88[‌888‌]). Mee eeeeeeee ee eeee eeeeeee eeee eeeeeeeeeee(η8-eeeeeeeeeeeeeeee)eeeeeeee(MM) (88) (eeeee 88)[‌888‌] eee eee eeeeeee eeeeeeee eeee eeeeeeeeeee(η8-eeeeeeeeeeeeeeee)eeeeeeeee(MM) (eeeeeeeeeee eeeeeeeeee), eeeeeeeeeeeeee, eee eeee (eeeee 88)[‌888‌] eeee eeeeeeee eeeeee eeeeeeeeeeeee eeeeeee. Mee eeeeeeeeeeeee ee eeeeeeeee eee eeeeeee eeeee eee-eeeeeeeeee eeeeeeee eeeeeeeee eeeeeeeee ee eeee eeeeeeee (eeeeeee 88,[‌888‌] 88,[‌888‌] eee 88[888,888). Meeeeeeee eeeeeeeeeeeee ee eeeeeeeee ee eee eeeeeeee ee eeeeeee ee eeeeeeee eeee eee eee ee eee Meeeee eeeeeee 888 eee eeeee eeeeeeeeeeeeeeeeee eeeee eeeeeee (eeeee 8),[‌888‌] eee eeee eee eee ee eeeeeeeeeeeee/eeee ee eeeeeeeeeee eeee eeeeeeeeeeeeeeeee (eeeee 8)[‌888‌,‌888‌] ee eeeeeeee(MM) eeeeeeeeeeee (eeeee 8).[‌888‌]

References


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