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20.5.8.1.9 Method 9: Aldol Condensations

DOI: 10.1055/sos-SD-020-01010

Westbrook, J. A.; Schaus, S. E.Science of Synthesis, (2007201110.

Enolates derived from ketones and esters undergo aldol-type condensations with oxalates to form α-oxocarboxylic esters. Some representative reactions in which diethyl oxalate is used to trap the enolate are summarized in Table 11.[‌4‌,‌107‌‌110‌]

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Meeee Meeeeeee Meeeeeee Meeeeeeeee Meeeeee Meeee (%) Mee
8 MeM, eeeeeee, 88°M, 8e 88 [‌888‌]
8 Me, MeMM, eeeeee, 8.8e 88 [‌888‌]
8 Me, MeMM, ee, 88e 88 [‌888‌]
8 Me, MeMM, 8°M, 88e 88 [‌8‌]
8 MeM, eeeeeee, ee, 88e 88 [‌888‌]

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Meeee [8-(eeee-Meeeeeeeeeeeee)-8-eeeeeee-8,8,8,8-eeeeeeeeeeeeeeeee-8-ee](eee)eeeeeee ­(Meeee 88, Meeee 8):[‌8‌]

Meeeeee eeeeeee (88.8e, 888eeee) eee eeeee ee 8°M ee e eeeeeee eeeeeeee eeee ee MeMMe, eeeeeeee ee eee eeeeeeee ee Me (8.88e, 888eeee) ee eeeee MeMM (888eM). Meeee eee eeeeeeee, 8-(eeee-eeeeeeeeeeeeee)eeeeeeeeee-8-eee (88.8e, 888eeee) eee eeeeeeeeee, eee eeeeeee eee eeeeeee eee 88e, eee eeee eee eeeeee MeMM eee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeee eeee Me8M (888eM), eeeeee ee 8°M, eee 8M MMe (888eM) eee eeeee eeeeee eeeee eeeeee eeeee eeeeeeeee eeee eee eeeeeee eee eeeeee. Mee eeeeeee eeeee eee eeeeeeeee, eeeeeeeee, eee eeeeee eeee M8M (8 × 888eM), eee eeee eeee eeeee (888eM). Mee eeeeeee eeeee eee eeeeeeeee, eeeee, eee eeeeeeeeeeee, eee eee eeeeeee eee eeee eeeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee/MeMM 88:88:8) ee eeee ee eeeeee eee; eeeee: 88.8e (88%).

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