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Stereochemistry of directed lithiation of 1,1′-bis(methoxymethyl)ferrocene

✍ Scribed by Russell C. Petter; Craig I. Milberg

Book ID
104244568
Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
327 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

1 ,l'-Bis(methoxymetbyl)ferrocene undergoes stereoselective directed dilithiation in the presence of t-butyllitbium. Evidence is presented to establish the stereochemistry of the products.

As part of a program of research directed toward potentially allostericl ferrocene-dicoronand hosts (e.g., l), we have need of efficient routes to tetrasubstituted ferrocene derivatives to act as central molecular pivots. Stereochemical control of the substitution pattern around the ferrocene nucleus is important in that different stereoisomeric ferrocene-dicoronands may lead to profoundly different allosteric interactions. Analogous metallocene-monocoronands are known to bind various ions with accompanying changes in dihedral angle about the central axis of the metallocene?

📜 SIMILAR VOLUMES

Highly diastereoselective ortho-lithiati
Highly diastereoselective ortho-lithiation of 1,1′-bis-(oxazolinyl)ferrocene directed to C2-symmetric chiral ligands
✍ Wanbin Zhang; Yoichi Adachi; Toshikazu Hirao; Isao Ikeda 📂 Article 📅 1996 🏛 Elsevier Science 🌐 English ⚖ 572 KB

C2-Symmetric 1, l',2,2'-tetrasubstituted ferrocene derivatives are prepared in high yields from chiral 1,1'-bis(oxazolinyl)ferrocenes v/a diastereoselective o,o'-dilithiation with sec-butyUithium followed by nucleophilic substitution. 1, l'-Bis(oxazolinyl)ferrocenes were prepared from 1,1 '-ferrocen