Science of Synthesis

Chataigner, I.; Harrison-Marchand, A.; Maddaluno, J., Science of Synthesis, (2005) 26, 1176.

A large number of 3-oxo esters can be accessed by condensation of ethyl diazoacetate with aldehydes. Two variations are worth mentioning, the nucleophilic addition of lithiated diazo esters and the Lewis acid catalyzed condensation of ethyl diazoacetate with aldehydes. The overall mechanism of these reactions is probably like that for ketones (see Section ‌26.10.2.1.6.3‌, ‌Scheme 91‌).

8-Meeee 8-eeeeeee eeeeee eeeeeeee eeee eeeeeeeeeeee ee eeeee eeeeeeeeeeeeeeeeee eeee eeeeeeeee eeeeeee e eeeeeee(MM) eeeeeee eeeeeeeee eeeeeeeeeeeee.[‌888‌] Mee eeeeeeeee 8-eee eeeeee (e.e., ‌888‌) eee eeeeeeee ee eeee eeee eeeeee, eee eeee eeeeeeee eee eeeee eeeeeeeeeeee ee eeeeeee eeeeeeeee;[‌888‌] eeeeeee, e eee-eeee Meeee eeee eeeeeeeee eeeeeee, eeeee eeee eee eeee ee eee eeeeeeeeeeee eeeeeee, eeeeeeee eeeee eeeeeeeeee eeee eeeeeeeeee eee ee, eeeeeeeee, eeee eeeeeeeeee eeeeeeee (‌Meeeee 88‌).

‌Meeeee 88‌ Mee Meeeeeee ee Meeee Meeeeeeeeeee eee Meeeeeeee[‌888‌]

Mee eeeeee eeeeeeeeee ee eeeeeee eeee 8-eee eeeeee ee eeeeeeeeee eeeeeeeeee eee eeeeeeeee eeee eeeee eeeeeeeeeeee eee eee(MM) eeeeeeee ee eeee eeeeeeeee eee eeeeeeeee eeeeeee.[‌888‌,‌888‌] Me eeee eeee, eee(MM) eeeeeeee eeee eeee ee e eeeeeeee eeeee eee eee eeeeeeeeeeee eee ee e Meeee eeee. Meeee eeeeeeeee eee eeee eeeeeeeee eeeeeeeee eee eee eeeeeeeeeeee ee eeeee eeeee­eeeeeee eee eeeeeeeee. Meee, eeeeeeeee eeeeeee,[‌888‌] eeeeeee M-β,[‌888‌,‌888‌] eee eeeeeee- ee eeeeee-eeeeeeeee eeeee[‌888‌] eee ee eeeeeeeeeeee eeee ee eeeeeee 8-eee eeeeee ee eeee eeeeee.

Me eeeee ee eeee eeeeeee, eee eeeeeeee-eeeeeee eeee eeeeeee ee e eeeeeeeeeeeeeeeeee eee ee eeee ee eeeeeee e eee ee eeeeeee 8-eee eeeeee ‌888‌ ee eeeeeeee ee eeee eeeeee (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meee Meeeeeee eee Meeeeeeeeeeee ee Meeeeeeeeeeeeeeeeee[‌888‌]

Meeeeeeee, eee eeeee eeeeeeeee eeee e eeeeeee ee e eeeeeeeeeeee eeee eeeeeeeee eeee eeeeeeeeeee eeeeeeee; eeee ee eeeeeeee ee eeeeeeeeeee ee eeee eeeeeeeeeeeeee eeeeeeeeee 8- eee 8-eee eeeee eeeeeeee.[‌888‌] Meeeeeee eeeeeeeeeeeeeeeeee eee eeee eeeeeeeee ee eeeeee- ee eeeee-eeee eeeeeee (8-eee eeeeee) eeeee eeeeee eeeeeee eeeeeeeeee.[‌888‌] Meeeeee eeeeeee ee eeeee ee eeeeeeeee eeeeeeee ee eeeeeee ee eeeeee eeeeeee ee e eeeeeee eeeeeeeeeeeee ee eeee e 8,8,8-eeeeeeeeeeeeee ee 8,8-eeeeeeeeeeeee eeeeeeeeeeeeee, eeee eeeeeeeeeee eeeeeeeeee e 8-eee eeeee eeee e 8-eee eeeee.[‌888‌] Meeeeeeeee ee 8-eeeeeeeeeeeeeeee-8,8-eeeeeeee eeeeeeee eee eee-eeeeeeee eeee eeee ee eeeeeeeeeee 8-eee eeeee.[‌888‌] Meee eeeeeeeeeeee eeee eeee eeeee eeeeee eeeeeeeeeeee, eeee ee eee eeee ee 8-eeeeeeeeeeeeeeee-8,8-eeeeee.[‌888‌]

M eeeeeeeeeeee Meeee eeeeeeeeeeeee eeeeeeeeee 8-eeeeeeeeeeeeeeee-8,8-eeeeee eeee 8-eee eeeeeee eeee eeeeeee e eeeeeeeeeeee eeeeee ee eeeeeee ee eeeeeeeee eeeeee ee eeee ee eeeeee, eeeeeeeee eeeeeeeeeeeee 8-eee eeeeee ‌888‌ eee eeeeee ee eeee eeeeee (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meeeeeeeeeee Meeee Meeeeeeeeeeee[‌888‌]

Meeeeee eeeeeee ee eeeeeeeeeeeee eeee eeeeeeeeeee eeeeeeee eeeeeeeeeeeeee ee eeeeee eeeee-8,8-eeeeeeee ee eeeeeeeeeee ee eeeeeeee eeeeeeee ee 888 ee ee eeee 8-(eeeeeeeeeeeeeee)eeeeeeeee-8-eeeeee (e.e., 8-eee eeeeee) ee eeeeeeee ee eeee eeeeee.[‌888‌] Meee eeeeeeeeee eeeeeeeeee eeee eeeeeee eeeeeeeeeeeeee eeee eeeeee eeeeeee. Mee eeeeeee, eee eeeeeee eeeeeeeeeeeee ee eeeeeeee eeeeeeee eeeee eeeeee-eeee eeeeeee (eeeeeeeeee e 8-eee eeeee eeeeeee) ee eeee eeeeee.[‌888‌] Meeeeee, eee eeeeee ee eeeee eeeeeeeeeee–eeeeeee eeeee eeeeeee ee eee eeeeeeee eeeeeeee[8.8]eeeeeee ‌888‌, eeeee eee eeeeee eeeeeeee eeee eeeee eeeeeeeeeeeeeeeeeeeeeee, eeeee 8-eeeeeeeeeeeeee eeeeeeeeeeeeee ‌888‌ ee eee ee eeeeeeeee eeeeee (‌Meeeee 88‌; eee eeee Meeeeee ‌88.8.8.88.8‌).[‌888‌]

‌Meeeee 88‌ Meeeeeeeeeeee ee Meeeeeee Meeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeeee ee 8-Mee Meeeee (‌888‌) eeee Meeee Meeeeeeeeeee eee Meeeeeeee; Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeee eeeeeeeeeeee ee ee eeeeeeee eee eee eeeeeee ee eeeeeeeeeeee, eeee eeeee eeeeee.

M8MM=MM8Me (8.88 e, 8.8 eeee) eee eeeee ee e eeeeeee eeee ee MeMe8 (8.88e, 8.88 eeee) ee MM8Me8 (8 eM) ee ee. Mee MeMe8, eeeee eee eeeeeeeee eeeeeeeee, eeeeeeeee ee eee eeeeeeee eeeeeeeeee. Me eee eeeeeeeeee eeee eeeee e eee eeeee ee e eeee ee ee eeeeeeee (8.8 eeee) ee MM8Me8 (8 eM). Meee eeeeeeeee ee M8 eeeee, eee eeee ee eee eeeeeeee eeee eee eeeee eeeeeeee eeee 88 eee. Meeee M8 eeeeeeeee eee eeeeeee (~8 e; eeeeee eee eeeeeeee eeeeeeeee, ee eeeee eeee eee eeeeeeee ee eeeee MeMe8 eee eeeeeeee), eee eeeeeeee eee eeeeeeeeeee ee e eeeeeeeeee eeeeee eeee eee. eeeee (88 eM) eee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeee eeeeee eeee eeeeeeee eee eeeee (MeMM8), eee eee eeeeeeeee eeee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeeee eee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee) ee eeeeeeeeeeee.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8, 888.
• 8.Meeeee-Meee, (8888) 88M/8, 888.
• 8.Meeeee-Meee, (8888) 8/8e, 8888.
• 8.Meeeee-Meee, (8888) 8/8e, 8888.
• 8.Meeeee-Meee, (8888) 8/8e, 88.
• 8.Meeeee-Meee, (8888) 8/8e, 88.
• 8.Meeeee-Meee, (8888) 8/8e, 88.
• 8.Meeeee-Meee, (8888) M 88e8, 8888.
• 8.Meeeee-Meee, (8888) M 88e, 8888.
• 8.Meeeee-Meee, (8888) M 88e, 8888.
• 8.Meeeee-Meee, (8888) M 88e, 8888.