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Please login or sign up for a free trial to access the full content. Variation 2: Reaction of [(Ethoxycarbonyl)iodomethyl]triphenylphosphonium Iodide with Aldehydes

DOI: 10.1055/sos-SD-020-01178

Evano, G.Science of Synthesis, (2007201269.

Alk-2-ynoic acid esters can also be prepared from aldehydes using modified ylides. Initially, Wadsworth and Emmons showed that the condensation of benzaldehyde with iodophosphonate 57, prepared in situ, allowed for the isolation of the alk-2-ynoic acid ester 45 without isolation of the intermediate vinyl iodide (Scheme 24).[‌155‌]

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Meeeeeeeeeee, Meeeeeee eee Meeee eeeeeeeee e eee-eeee eeeeeeeee ee [(eeeeeeeeeeeeee)eeeeeeeeee]eeeeeeeeeeeeeeeeeeee eeeeee (88) eeee eeeeeeeeeeee eeeeeeeee [(eeeeeeeeeeeeee)eeeeee]eeeeeeeeeeeeeeeeeeee eeeeeee (88). Meee eeeeeee ee eeeeeeeee ee eee eeeeeeeeee ee eeeeeeeee eeee eee-8-eeeee eeee eeeeee. Mee eeeeeee eeeee ee eee eeeeeeee eeeeeeee eee eee eeeeeeeeeeee 88, eeeee eeeeee eeee eeeeeeeee ee eeee α-eeee-α,β-eeeeeeeeeee eeeeee 88. Meeee eee eeeeeee eeeeeeeeeeeeeeee eeeee eeeee eeeeeeeeee ee eeee eee eee-8-eeeee eeee eeeeee 88 (Meeeee 88).[‌888‌] Mee eee ee eeeeeee 88, eeeee eee ee eeeeee ee eee eeee ee 8°M, eeeee eeee eeeeee ee eee-8-eeeee eeee eeeeee eeeee eeee eeeeeeeeee.

Meeeee 88 Meeeeeeee ee Mee-8-eeeee Meee Meeeee eeee [(Meeeeeeeeeeeee)eeeeeeeeee]eeeeeeeeeeeeeeeeeeee Meeeee eee Meeeeeeee[‌888‌]

Meeeeeeeeee 88

M8 Meeee (%) ee 88 Mee
Me 88 [‌888‌]
8-MeMM8M8 88 [‌888‌]
8-MeMM8M8 88 [‌888‌]
8-MMM8M8 88 [‌888‌]
8-eeeeeeee 88 [‌888‌]
8-M8MM8M8 88 [‌888‌]
8-M8MM8M8 88 [‌888‌]
MM=MMMe 88 [‌888‌]
(MM8)8Me 88 [‌888‌]
MM=MMe(MM8)8MM=MMe8 88 [‌888‌]
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Meeeeeeeeeee Meeeeeeee

[(Meeeeeeeeeeeee)eeeeeeeeee]eeeeeeeeeeeeeeeeeeee Meeeee (88):[‌888‌]

Me e eeee ee [(eeeeeeeeeeeeee)eeeeee]eeeeeeeeeeeeeeeeeeee eeeeeee (88; 88.8e, 8.888eeee) eee M8MM8 (8.88e, 8.888eeee) ee MeMM (88eM) eee eeeee ee 88°M eeeee eeeeeeee eeeeeeee e eeee ee M8 (8.88e, 8.888eeee) ee MeMM (88eM). Meeee 8e ee eeee eeeeeeeeeee, e eeeeee eeeeeeeeeee eeeeee; eee eeeeeee eee eeeeee ee ee, eee eee eeeeeeeeeee eee eeeeeeeee ee eeeeeeeeee eee eeeeee eeee eeee MeMM (888eM). Mee eeeee eeeeeee eee eeeeeee ee M8M (8 × 888eM) eeeee eee M8M eeeeeeee eeeeeee, eeeeeeee, eee eeeeee ee eee eeee ee 8°M; eeeee: 88.8e (88%); 8M MMM (MMMe8/MMMM-e8, δ): 8.88 (e, 8M, M=8.8Me), 8.88 (e, 8M, M=8.8Me), 8.88 (e, 8M), 8.888.88 (e, 88M).

Meeee Meee-8-eeeeeee 88; Meeeeee Meeeeeeee:[‌888‌]

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