Stereoselective alkylation of chiral glycine enolate synthons. The enantioselective synthesis of α-amino acid derivatives.
✍ Scribed by Joseph F. Dellaria Jr.; D.Santarsiero Bernard
- Publisher
- Elsevier Science
- Year
- 1988
- Tongue
- French
- Weight
- 293 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The highly stereoselective alkylation (% de=99.6 to 97.6) of a new chiral glycine enolate synthon derived from D-2-phenylglycinol is described. Deprotection of the alkylation adducts in a one-pot, three-step procedure provides the ethyl ester hydrochloride salts of the corresponding a-amino acids with no attending racemization.
📜 SIMILAR VOLUMES
For the purpose of practical preparations of a variety of enantiomerically pure uncommon ¢x-amino acids, alkylations of the chiral glycine equivalent 5, which possesses axially chiral binaphthol as an auxiliary, with several electrophiles were investigated. The alkylation proceeded smoothly in satis
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Nucleophilic addition of the chiral lithium enolates of (S)-(-)-4-benzyl-2-oxazolidinone acetamide with N-tosyl arylaldehyde imines gives b-aryl-b-amino acid derivatives in good yields and excellent diastereoselectivity.