Sumnary: trans-2,5-Bis(methoxymethyl)-and trans-2,5-bis(methoxymethoxymethy1)pyrrolidines proved to be excellent chiral auxiliaries for the asymmetric alkylation of the corresponding carboxyamide enolates giving good chemical yield and high stereoselectivity (invariably over 95% de), with remarkable
Asymmetric aldol reaction of amide enolates bearing trans-2,5-disubstituted pyrrolidines as chiral auxiliaries
โ Scribed by Tsutomu Katsuki; Masaru Yamaguchi
- Publisher
- Elsevier Science
- Year
- 1985
- Tongue
- French
- Weight
- 244 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
Condensation of aldehydes with Zr enolate of chiral N-propionyl-trans-2,5_disubstituted
pyrrolidine proceeded with high diastereo-and diastereofaceselection. Stereoselectivity in the reaction of the corresponding N-acetyl compounds was also examined.
๐ SIMILAR VOLUMES
C2,33Wittig rearrangement of (2S,SS)-N-(alkenyloxyacetyl)-2,5-bis-(methoxymethoxymethyl)pyrrolidine enolate was Studied and zirconium enolates of the corresponding (E)-alkenyloxyacetyl compounds were found to rearrange with high syn-diastereo and diastereoface selection. In contrast to the stereoche
Highly diastereoselective alkylation (296% de) of a-lithiated N-[N'-bis(methylthio)---methyleneglycyl~-~-2,5-bis~methoxymethoxymethyl~pyrrolidine and subsequent hydrolysis gave a-amino acids of high optical purity. An unusual amino acid (2S,9\_S)-2-amino-8-oxo-9,10epoxydecanoic acid was synthesized