✦ LIBER ✦
Enantioface differentiating Michael reaction of ethyl acetoacetate with alkylidenemalonates via chiral enamine
✍ Scribed by Kiyoshi Tomioka; Kōsuke Yasuda; Kenji Koga
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 253 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
Utilizing the I_-valine-based chiral lithioenamine (5) of ethyl acetoacetate (l), enantioface differentiating Michael reaction with alkylidenemalonates (2) gave, after decarboxylation, B-substituted g-keto esters (3) in a fair to good enantiomeric excess. Kinetic diastereoenrichment of the initial Michael adducts (7) was also studied. Combination of both processes provides the procedure for the synthesis of 3 in 55-93% ee.