You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via20.5.14.1.4.5 Variation 5: Alkenation of α-Oxo Esters
Please login to access the full content or check if you have access via
Vanderwal, C. D.; Jacobsen, E. N., Science of Synthesis, (2007) 20, 1325.
The alkenation of α-oxo esters is a very general method for the introduction of the alk-2-enoic acid ester function. The alkene synthesis can make use of many different methods, including aldol condensation, Wittig and Horner–Wadsworth–Emmons reactions. The condensation of methyl glyoxalate with pyranone 115 proceeds in good yield to produce alk-2-enoic acid ester 116 as the single geometrical isomer (Scheme 21).[73] An intramolecular variant of this aldol condensation reactivity enables the synthesis of alk-2-enoic acid ester 118 from methyl ketone/α-oxo ester 117 in high yield.[74]
Meeeee 88 Mee-8-eeeee Meee Meeeee ee Meeeeeeeeeeee ee α-Mee Meeeee[88,88]
Meeeeeeeeeee Meeeeeeee
Meeeee (8M)-{(8M,8M)-8-Meeee-8-[8-(eeee-eeeeeeeeeeeeeeeeeee)-8,8-eeeeeeeeeeeee]-8-eeeeee-8-eeeeeeeeeeeee-8M-eeeee-8-eeeeeee}eeeeeee (888):[88]
Me e eeee ee eeeeee 888 (8.88 e, 8.88 eeee) ee MeMM (88 eM) eee eeeee M8MM8 (8.88 e, 88.8 eeee) eee 8.8 M eeeeee eeeeeeeeee ee MMM (88.8 eM, 88 eeee). Mee eeeeeeeee eeeeeee eee eeeeeee eee 88 eee, eee eeee eeeeee eeee e eeeeeee ee eee. ee MM8Me (888 eM) eee Me8M (888 eM). Mee eeeeeee eeeee eee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee Me8M (888 eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeee ee eee eeeee eeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/MeMMe 88:8) eeeeeeee eeeee 888 ee e eeeeee eee, eeeee eeeeeeeeee eeee eeeeeeee; eeeee: 8.88 e (88%).
References
[73] | Meeeee, M. M.; Meeeee, M. M.; Meeeeee, M. M.; Me, M. M.; Meeeeee, M. M.; Meeeee, M. M.; Meeee, M. M.; Mee, M.; Meeôee, M.; Meeee, M.; Meee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 888, 88888. |
[74] | Meeee, M. M.; Meeeee, M.-M.; Meeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8e8, 888.