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Synthesis of dipeptides containing α-substituted amino acids; their use as chiral ligands in Lewis-acid-catalyzed reactions

✍ Scribed by Bernard Kaptein; Vania Monaco; Quirinus B. Broxterman; Hans E. Schoemaker; Johan Kamphuis


Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
949 KB
Volume
114
Category
Article
ISSN
0165-0513

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✦ Synopsis


Abstract

L‐α‐Methylphenylalanine, obtained by enzymatic resolution of the corresponding racemic amide with amidase from Ochrobactrum anthropi NCIMB 40321, was used in the synthesis of dipeptides containing α‐substituted amino acids. The 2‐hydroxynaphthalene‐1‐carboxaldehyde Schiff bases of the dipeptides (1 and 2) were tested as Ti(IV) and Al(III) complexes in asymmetric Lewis‐acid‐catalyzed reactions. Only the Al(III) complex of 2 showed moderate enantioselectivity in the cyanation reaction of benzaldehyde with TMS‐CN.


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ChemInform Abstract: Synthesis of α-Subs
✍ Gangadhar Nagula; Vincent J. Huber; Christopher Lum; Burton A. Goodman 📂 Article 📅 2001 🏛 John Wiley and Sons ⚖ 31 KB 👁 1 views

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