You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via20.2.4.1.6.2 Variation 2: Homocouplings Mediated by Iodine
Please login to access the full content or check if you have access via
Masse, C. E., Science of Synthesis, (2007) 20, 346.
Rapid entry into the preparation of racemic or meso-2,3-disubstituted succinic acids can be accomplished via the oxidative coupling of carboxylic acid dianions mediated by halogens. A representative example of this approach utilizes 2-alkyl- and 2-arylacetic acids in the presence of iodine as the oxidant.[16] Treatment of a series of these substrates 19 with lithium diisopropylamide in tetrahydrofuran affords the carboxylic acid dianions 20, which, upon treatment with 0.5 equivalents of iodine in tetrahydrofuran, afford the 2,3-disubstituted succinic acids 21 with high levels of conversion (Scheme 11).
Meeeee 88 Meeeeeeeeeee ee eee Meeeeeeee Meeee ee Meeeeeee Meeee[88]
Meeeeeeeeeeee, eee eee ee 8.8 eeeeeeeeeee ee eeeeee ee eeeeeeee ee eee eeeeeeeee eeeeeeee. Meeeeeeee ee eeeeeeeeeeee 88 eeee 8.8 eeeeeeeeee ee eeeeee eeeee ee eee eeeeeeeee ee eee 8-eeeeeeeeee eeee eeee eeeeee ee eeee ee eee eeeeeeee eeeeeee eeeeeeee. Me eeeee ee eee eeeeeeeeeeeeeee ee eee eeeeeeee, 8,8-eeeeeeeeeeeeeeee eeee (88, M8 = Me) ee eeeeee ee e eee/eeee eeeee ee 88:8. Me ee eeeeeeeee eeee eee eeeeeeee eeeee eeeee eee e eeeeeee eee eeeeee eeeeeee eee eeeeeeeeeee eeeeeee, eeeee eeeeeeeee eee eeeeeeeeee ee eee eeeee α-eeeeeeeeeeee.
Meeeeeeeeeee Meeeeeeee
8,8-Meeeeeeeeeeee Meeeeeee Meeee 88; Meeeeee Meeeeeeee:[88]
Me e eeee ee 88 (8.8 eeeee) ee MMM (8.8 M) ee −88°M eee eeeee MMM (8.8 eeeee) eee eee eeeeeee eee eeeeeee eee 88 eee. Mee eeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeeeee eee eeeee eeeeeeeee eeee 88 ee ee eee-eeeee eeeeee. Meeeeeeee eeee 88 eee eeeeeeeee ee MMM (8.8 M) eee eeeeee ee −88°M eeeeeeee ee eeeeeeee ee M8 (8.8 eeeee). Mee eeeeeee eee eeeeeee ee −88°M eeeeeeeee, eeee eeeeeee eeee M8M, eee eeeeeeeee eeee 8 M MMe. Mee eeeeeee eeeeee eeee eeeeeeeee, eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeeeee eee eeeeeeee eeee 88; ee (88, M8 = Me) 888–888°M.
References
| [16] | Meeeeeeee, M. M.; Meeeeeee, M. M.; Meeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8e, 888.
- 8.Meeeee-Meee, (8888) M 8-8, 888.
Return to Top