Synthesis and NMR spectroscopic studies of optically active derivatives of γ-aminobutenoic acids and 2-amino-pyrrolin-4-ones
✍ Scribed by Margarita Petroliagi; Olga Igglessi-Markopoulou
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 2001
- Tongue
- English
- Weight
- 53 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
An efficient method for the preparation of optically active derivatives of γ‐amino‐butenoic acids and their cyclic derivatives, 2‐amino‐pyrrolin‐4‐ones, from α‐amino acids is described. Partial racemization accompanies the formation of initial unsaturated γ‐amino‐β‐hydroxy esters 5–8, as determined by chiral HPLC.
📜 SIMILAR VOLUMES
## Abstract The synthesis of a series of optically active __N__‐acetyl butenoates **3–5** is described using a facile methodology. These butenoates undergo cyclization to the corresponding __N__‐acetyl‐2‐alkyl‐pyrrolin‐4‐ones **6,7** retaining their stereochemical integrity. The structure of the ne
## Abstract An efficient method for the preparation of novel cyano derivatives of 4‐amino‐3‐hydroxybutenoic acids **4–8** and __N__‐substituted‐2‐aminopyrrolin‐4‐ones **9–18** is described; the structure of compound **13** has been elucidated with X‐ray analysis.
## Abstract The reaction of (+)‐car‐2‐ene (**4**) with chlorosulfonyl isocyanate (=sulfuryl chloride isocyanate; ClSO~2~NCO) led to the tricyclic lactams **6** and **8** corresponding to the initial formation both of the tertiary carbenium and __α__‐cyclopropylcarbenium ions (__Scheme 2__). A numbe