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Diastereoselective additions of organolithium reagents to the CN bond of protected erythrulose oxime ethers. Synthesis of enantiopure α,α-disubstituted α-aminiacids

✍ Scribed by J.Alberto Marco; Miguel Carda; Juan Murga; Florenci González; Eva Falomir

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
252 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

The addition of organolithium reagents to the C=-N bond of several cnflhrulosc-dcflved chiral (E)and (Z)-ketoximc ethers has been shown to be highly diastereoselectivc for the (E)-isomers. A chelated transilion state has been p~sed to explain this n~ult The addition products were converted into the two c~,~-disub~tuted ¢-aminoacids (R)-2-(--}-methyisedne and .(R)-(+)-2-phenylsedne.

📜 SIMILAR VOLUMES

ChemInform Abstract: Diastereoselective
ChemInform Abstract: Diastereoselective Additions of Organolithium and Organomagnesium Reagents to the C=N Bond of a Chiral, Cyclic Nitrone Derived from Erythrulose.
✍ J. A. MARCO; M. CARDA; J. MURGA; R. PORTOLES; E. FALOMIR; J. LEX 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 34 KB 👁 1 views

## Diastereoselective Additions of Organolithium and Organomagnesium Reagents to the C=N Bond of a Chiral, Cyclic Nitrone Derived from Erythrulose. -Compound (III), whose structure is determined by X-ray analysis, is unreactive towards organometallic reagents either in the presence or absence of