(L)-pyroglutamic acid as a chiral starting material for asymmetric synthesis
β Scribed by Jack E. Baldwin; Mark G. Moloney; Sung Bo Shim
- Book ID
- 104216108
- Publisher
- Elsevier Science
- Year
- 1991
- Tongue
- French
- Weight
- 122 KB
- Volume
- 32
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Elaboration of lactam (1). readily available from &)-pyroglutamic acid, provides access to a range of 2,4-and 2,3,4-substituted pyrrolidinones.
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For the preparation of L-iduronic acid, trehalose was converted into a derivative of a novel disaccharide, B-Lidopyranosyl I~-L-idopyranoside, through diastereoselective hydroboration of the 5, 5'-di-eno intermediate. The 6-and 6'-hydroxy groups were then oxidized in two steps to give a disaccharide
The synthesis of four enantiopure hydroxyamidines is amidine was obtained by coupling of an (S)-malic acid derived N-acyliminium ion with Ξ²-naphthol. The other described. One amidine was obtained from (S)-pyroglutamic acid. Its key step involved the addition of phenylmagnesium amidines were obtained