Schöllkopf Bis-Lactim Ether Method
(Schöllkopf Bis-Lactim Method)
Published Online: 15 SEP 2010
Copyright © 2010 John Wiley & Sons, Inc. All rights reserved.
Comprehensive Organic Name Reactions and Reagents
How to Cite
2010. Schöllkopf Bis-Lactim Ether Method. Comprehensive Organic Name Reactions and Reagents. 570:2523–2528.
- Published Online: 15 SEP 2010
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The Schöllkopf bis-lactim ether mediated synthesis of chiral nonproteinogenic amino acid is known as the Schöllkopf bis-lactim ether method. In addition, the reaction between a lithiated Schöllkopf bis-lactim ether and an electrophile is termed as the Schöllkopf alkylation, while the addition of such lithiated intermediate to an αβ-unsaturated compound is referred to as the Schöllkopf-type addition. It has been reported that addition of 2,6-di-tert-butylpyridine produces smooth reaction for the preparation of the Schöllkopf bis-lactim ether. Such stereochemical outcome for the Schöllkopf alkylation is known as the Schöllkopf's rule or Schöllkopf's observation. However, this rule is not always followed, and the reaction is probably controlled by both the reagent and substrate. It has been observed that complete hydrolysis of the Schöllkopf bis-lactim ether take place in presence of concentration of HCl, rather than mild acidic conditions. This reaction is very useful for the preparation of unnatural, nonproteinogenic amino acids.
- bis-lactim ether;
- diethyl ether;
- methyl iodide;
- trans/cis ratio