Abstract
An optically active form (≥ 98% ee) of N-(ortho-tert-butylphenyl)-5- methoxymethyl-2-pyrrolidinone 3 having axial chirality was prepared from ortho-tert-butylaniline and (S)-5-(methoxymethyl)butylolactone in short steps and a completely stereoselective manner. The reactions of Li-enolate from lactam 3 with various electrophiles proceeded with 3,5-cis-selectivity.
| Original language | English |
|---|---|
| Pages (from-to) | 1949-1952 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 40 |
| Issue number | 10 |
| DOIs | |
| Publication status | Published - 1999 Mar 5 |
Keywords
- Axial chirality
- Diastereoselective reaction
- Enolate
- Lactam
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Fujita, M., Kitagawa, O., Izawa, H., Dobashi, A., Fukaya, H., & Taguchi, T. (1999). Stereoselective synthesis of an optically active axially chiral lactam and its reaction with some electrophiles. Tetrahedron Letters, 40(10), 1949-1952. https://doi.org/10.1016/S0040-4039(99)00051-9