Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content.
26.10.2.1.2.2 Variation 2: With Carboxylic Acids, Anhydrides, or Esters

DOI: 10.1055/sos-SD-026-01067

Chataigner, I.; Harrison-Marchand, A.; Maddaluno, J.Science of Synthesis, (2005261151.

The route to oxo esters based on electrophilic acylations using esters and their analogues is so general (it encompasses the Claisen and the Dieckmann condensations) that it cannot be fully covered within this limited framework. The examples presented here are chosen in an attempt to update reference papers on the topic,[‌281‌‌283‌] which should be consulted for detailed coverage of early work. The Dieckmann annulation will be examined separately (see Section 26.10.2.1.7.1). Note also that the widely used synthesis of acetyl­acetamides by the addition of primary or secondary amines to diketene is not relevant to this section.

Mee Meeeeee eeeeeeeeeeee ee eee eeeee eeeeeeee ee eee eeeee eeeeeeeeeeee. Meeeeeeeee, eeee eeeeeeee eeeeeeee eee eeee-eeeeeeeeeeee ee eeeeee, eee ee eeeeee eeeeeeeeeeeee eeeeeeeeeee eeee ee eee eeeeeee ee eee eeeee-eeeeeeeeeeee ee eeeeeeeee eeeeee. Mee ee eee eeee eeeeeeeeeeee eeeeeeeeeee eeee eee eee eeeee eeeeeeeee eee eeeeeeeee (eee eeee eeeeeee α-eeeeeeeee) ee eee eeeeeeeeee eeeeeee eee eMe eeeeee ee eeeee eeeeeeeee. Me eeee eeee, eee eeeeeeee eeeeeeee eeeeeee e eeeeee ee eeeeeeeeee eeee eeeeee eee eeeeee ee eee eeeeeee eeeeeee eee eeeeeee eeeeeeeeeeee eeeeeee ee eeeeeeeeee.

Meeeeee eeeeeeeeee eeeee eee eeeeeeeeee ee eeeeeeeeeee eee eeeeeeeeeeee eee eeeeeeeeeeeee eeeeeeeeee ee eeee eeeeeeeeee eeeee. Mee eeeeeeeeeeee ee eee eeeeeee (eeeeeeee ee eee eeeeeeee eeeeeeee ee e eeeee eeeeee eeeee) ee eee eeeeeeeeeeee eeeeee ee eee eeee eeeeeeee; eeee ee eeeeeee ee e eeeeeeee eeeeeee eeee eeee eeeeeee (eee Meeeeee 88.88.8.8.8.8). Mee eeeeeeee ee eeee 8.8 eeeeeeeeeee ee eee eeeee ee eee eeeeeee eee ee eeeeeeeee.[‌888‌] Mee eeeeeeeeeeee ee ee eeeeee ee eeeeeee eeee eee eeeee eeeeee eeeeee, eeeeeee ee eeeeeee eeeeeeeee, ee eeeeeeeeeeee eeeeeeeeeee. Meee eeeeeee eee ee eeeeeeeee ee eeeeee 8 eeeeeeeeeee ee eeeeeee eeeeeeee ee eee eeeeee ee eeeeeeeeeee eee 8-eee eeeee ee eeee ee ee ee eeeeee, eeee eeeeeeeeee e eeeeee eeeeeeee ee eee eeeeeee.[‌888‌] Meeeeeeee, eeee eee eeeeeeeeeeeee eeeee eeeeee eeeeeeee ee eeeeee eeee, eeeeeeeeeeeee eee ee eeeeeeeee eeeeee eee eeeeeeeeeeee ee eee eeeeeeeeeeee eeeeee, eeeeee eeee eee eeee eeee (eeeeeee eeeeeeeeeeeeeeee)[‌888‌] ee eee eeeeeeeee eeeee (eeeeee eeeeeee eee eeeeeeeeeeee), ee eeeeeeeee e eeeeeeee eeeeeeeee eeeeeeeeeee eeeeeeeee ee eee eeee eee eeeeeeeeeeee.[‌888‌] Mee eeeeeeee eeeeeee eee eeeee eee eee eeeeeee (eeeeeeeeeeeee) ee eeeeeee eeeeee eeee eeeeeeee eeee eee ee eeeeeee ee eeeee eeeee eeeee eeeeeeee, eeee ee eeee-eeeee eeeeeee eeeeeee.[‌888‌,‌888‌]

Meeeeeeee ee eeeeeeee eeeeeeeeeeee ee eeeeeee eee ee eeeeeeeee e eeee eeeeeeeeeeeeeee eeeeeee eee eMe eeeeee.[‌888‌] Meeee eee eeeee eeeeeee eeeeeeee eeee eeeee eeee eeeee[‌888‌] eeeeeeeeee ee eeee eee eeeeeeee 8-eee eeeeeeeeeee ee eeeeee ee eeee eeeeee.[‌888‌‌888‌] Meeeeee, eee eeeeeeeee ee eeeee/eeeee eeeeeee eeeeeeee eee eeee eeeeeeeee eeeeeeeeeeee eee ee eeeeeeeeee eeee eeeeeeee ee eeeeeee eeeeeeeeee, eeee ee eeeeeeeeeeeeeeee[‌888‌] (e.e., 88) (Meeeee 88) ee β-eeeeeee.[‌888‌]

Meeeee 88 Meeeeeeee ee Meeeeee Meeeeeee[‌888‌]

Meeeee[‌888‌,‌888‌] eee eeeeeeeee eeeeeeee eee eeee eeee eeeeee eeee eeeeee eee eeeeeeeeee, eeeeeee eeeeeeee eeeeeeee eeee ee ee eeee eeeeeeeee ee Meeeeee/Meeeeeeee eeeeeeeeeeeee, ee eeeeeeeeeee ee eee eeeeeeeee ee 8-eeeeee-8-eee eeeee 88 (Meeeee 88).[‌888‌,‌888‌]

Meeeee 88 Meeeeeee-Meeeeee Meeeeee Meeeeeeeeeee[‌888‌]

8-Mee eeeeee eeee eeee eeee eeeeeeee eeeeee e Meeeeee-eeee eeeeeeeeeeee ee eeeeeeeeeeee eeeeeeeee ee eeeeeeee(MM) eeeeeeee.[‌888‌] Meeeeeeeeeeeeeee eeeee eeeeeeee eeeeeee eeeeeeeee-8-eeeeeeeeeeeeee eee eeeeee eeeeeeeee eeeeeeee 8-eee eeeeee ee eeeeeeee ee eeee eeeeee.[‌888‌] Meee eeeeeeee eeeeee eeee e eeeeeee eeeeeeeeeeeeeeeeeeee eeee eeeeeee ee eee eeeeee eeeeeee ee eee eeeeeeeeeeeee.

Meeeeeeeee eeeeeeeee eeeeeeeee eeeeeeeee eeeeee eeeeee eeeeeeeeeeee. Meeeeee ee eeeeeeeee eeeee eeeeeeee eeeeeeee eeee β-eeeeee-eeeeeee M-eeeeee eeeeeeeeee ee eeeee eee eeeeeeee 8-eee eeeeeee, eeeeee ee eeeeee eeeeee.[‌888‌] Mee Meeeeeee eeeeeeee ee e eeeeeeeeee eeeee eeee eeeeeeee eeeeeeeeee eeeeeeee. Meeeeee ee eeeee eeeeeeeeeeeeee eeeeeeee eeeeeee ee eeeee eeeeeeeee eeeee eeeeeeeeeee eeee eeeeeee eeeeeeeeee (e.e., 88) ee eee eeeeeeee ee 8.88 eeeeeeeeeee ee eeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee,[‌888‌] 8.8% eeeeeeeee/eeeeee,[‌888‌] ee 88% eeeeee eeeeeeeeeeeeeeeeee[‌888‌] ee eeee eeee eeeeee ee eee eeeeeeee 8-eee eeeeee, e.e. 888 (Meeeee 88).

Meeeee 88 Meeeeeee Meeeeeeeee Meeeeeee[‌888‌]

Meeeeeeeeeeeeee(MM) eeeeeeeee (eee Meeeeee 88.88.8.8.8.8) eee eeee eeeeeeee eeeeee eeeeee.[‌88‌,‌88‌] Me eeeeeeeeeeeeee eeeeeee ee eee eeeeeeeee ee ee eeeee eeeeeee ee e eeeeeeeee eeeeeee ee eeeee eeeeee e eeeeeeeeee eeeeeeeeeeeee eeeeeeeee e eeeeee-eeeeeeeee eeee eeeeeeeeee α-eeee eeeeeeeeee eeee 8-eee eeeeee ee eee eeeeeeee ee eeeeeee eeeeee.[‌888‌] Meeeeeee, eeeeeee eeeeeee eeee ee eeeee eeeee eee e eeeeeeeee eeeee eee eeeeeee e eeeeeeeee eeeeeeeeeeeee ee eee eeeeeeee α ee eee eeeee ee ee eee eeeeeeeee, eeeeeeeee ee eee eeeeeeeeee (eeeeeee eeeeee, ee eeeeeeeee) ee eee eeee eeee. Me eee eeeee, e eeeeee 8-eee eeeee ee eeeeeeee eeeeeee e eeeeeeeee eeeeeeeeee eeeeeeee ee Meeee ee ee.[‌888‌]

M MeeeeeeMeeeee-eeee eeeeeeee ee eeeeee eeeeeeeee eee ee eeeeeeeeee 8-eee eeeee ee eee eeeeeeee eeeeeeeeeeeeeeee(MM) eeeeeeeeeeeeeeeeeeeeeeeeeee eeeee e 8,8,8-eeeeee eeeee.[‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeee (8M)-8-{[(Meeeeeeee)eeeeeeee]eeeee}-8-eee-8-eeeeeeeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

M 8.8M eeee ee MeM8M(MM8)8MeM ee MMM (8.88eM, 8.8 eeeee) eee eeeee ee e eeeeeee eeee ee eeeeeeeee 88 (8.88e, 8.8eeee) eee MeMe8(MMe8)8 (888ee, 88eee%) ee eeeeeee (88eM) eeeee eeeee ee ee. Meeee 88eee, Me8M (88eM) eee eeeee eee eee eeeeeeeeee eee eeeeeeee eeeeeee e eee ee Meeeee. Mee eeeeeeee eee eeeeee eeee 8M MMe, eee. MeMMM8, eee eeeee, eeee eeeee (Me8MM8). Meeeeeeeee eee eeeeeeeeeeeee ee eeeee eeee e eeeee eee eeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8); eeeee: 888ee (88%).

References