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Regio- and stereocontrolled preparation of α-substituted phosphonocrotonate derivatives

✍ Scribed by Geoffrey F. Solberghe; István E. Markó

Book ID
104251418
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
83 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

Under suitable reaction conditions, monoalkylation of triethyl phosphonocrotonate 11 could be efficiently accomplished, leading to the preparation of a-substituted phosphonates 15. The reaction is totally regioselective and completely (E)-selective. The novel phosphonocrotonate 19 underwent smooth Horner-Emmons condensation, producing a key-precursor for the synthesis of the middle core of the manzamine alkaloids.

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✍ Chih-Wei Chang; Stéphanie Norsikian; Regis Guillot; Jean-Marie Beau 📂 Article 📅 2010 🏛 John Wiley and Sons 🌐 English ⚖ 552 KB

## Abstract A process for highly effective regio‐ and stereoselective palladium‐catalyzed allylic substitution of 2,3‐unsaturated derivatives of __N__‐acetylneuraminic acid (Neu5Ac2en) has been developed. We show that the efficiency of the allylation reaction depends on suitable protecting groups o