Synthesis of β-cyanoalanine and enantiomerically enriched aspartate derivatives via the Zn- or In-mediated nucleophilic addition to α-imino esters
| Autor: | Makoto Yasuda, Nayyar Ahmad Aslam, Arya Jayadev Sudha, Srinivasarao Arulananda Babu, Akshey Sandhu, Akio Baba |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
Nucleophilic addition 010405 organic chemistry Chemistry Stereochemistry Organic Chemistry chemistry.chemical_element Zinc 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Stereocenter Enantiopure drug Derivative (finance) Drug Discovery Aspartic acid Alkyl |
| Zdroj: | Tetrahedron. 76:131217 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2020.131217 |
| Popis: | We report the synthesis of β-cyanoalanine derivatives and enantiomerically enriched aspartates. The zinc-mediated addition of α-bromoacetonitrile to α-imino esters afforded various β-cyanoalanine derivatives 3a-l and 5a-d in satisfactory to good yields. The zinc- or indium-mediated addition of α-bromoacetonitrile or ethyl 2-bromoacetate to enantiopure N-tert-butanesulfinyl α-imino esters gave the corresponding products 3m-p in satisfactory yields and diastereoselectivity. Notably, the indium-mediated addition of alkyl 4-bromocrotonates to enantiopure N-tert-butanesulfinyl α-imino esters gave the corresponding enantiomerically enriched β-vinyl aspartates 10c-e (aspartic acid derivatives) with high diastereoselectivity (syn isomers). The stereochemistry of the vicinal stereocenters of the compounds 10c-e (major isomers) were assigned based on the X-ray structure of a derivative 11d which was obtained from 10c. To show the utility of β-cyanoalanine and β-vinyl aspartate derivatives, representative β-cyanoalanine compounds 3a/3b, 5d and aspartic acid derivative 10c were subjected to selected synthetic transformations. |
| Databáze: | OpenAIRE |
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