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Decarboxylative Dehydration of β-Hydroxycarboxylic Acids by Redox Condensation: A Novel Olefin Synthesis

✍ Scribed by Dr. Johann Mulzer; Gisela Brüntrup

Publisher: John Wiley and Sons
Year: 1977
Tongue: English
Weight: 208 KB
Volume: 16
Category: Article
ISSN: 0044-8249
DOI: 10.1002/anie.197702551

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✦ Synopsis

2] The perturbation [(-I) effect] caused by the introduction of the nitrogen is compensated by the alkyl substituents [(+I) effect]: compensation of this perturbation results in a behavior analogous to that of the unperturbed system (ethylene).

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## Abstract A novel method for the asymmetric synthesis of __α__,__β__‐diamino acids by using the 2,3,4,6‐tetra‐__O__‐pivaloyl‐__β__‐D‐glucopyranosyl group (Piv~4~Glc) as chiral auxiliary was developed (__Table__ and __Scheme__). The reaction was promoted by CuBr⋅Me~2~S as __Lewis__ acid, and high