Abstract
The stereospecific synthesis (>99:1) of α‐alkylcarboxylic acids 3 has been achieved using chiral auxiliaries such as 1, which is a derivative of the Kemp triacid. Compound 1 is coupled at the imide group with the acid chloride 2. Lithiation (→enolate), alkylation, and cleavage leads to 3. The effectiveness of 1 is a consequence of the fact that it shields one side of the enolate from attack by the electrophile EX (examples: R Me, E PhCH2, or R PhCH2, E Me). (Figure Presented.)
| Original language | English |
|---|---|
| Pages (from-to) | 555-556 |
| Number of pages | 2 |
| Journal | Angewandte Chemie International Edition in English |
| Volume | 29 |
| Issue number | 5 |
| DOIs | |
| Publication status | Published - 1990 May |
All Science Journal Classification (ASJC) codes
- Catalysis
- Chemistry(all)
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Cite this
Jeong, KS. S., Parris, K., Ballester, P., & Rebek, J. (1990). New Chiral Auxiliaries for Enolate Alkylations. Angewandte Chemie International Edition in English, 29(5), 555-556. https://doi.org/10.1002/anie.199005551