Enantioselective  Michael  Addition of the 2‐(1‐Ethylpropoxy)acetaldehyde to  N ‐[(1 Z )‐2‐Nitroethenyl]acetamide – Optimization of the Key Step in the Organocatalytic Oseltamivir Synthesis | Zendy

Hajzer Viktória | Zendy; Latika Attila | Zendy; Durmis Július | Zendy; Šebesta Radovan | Zendy

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Enantioselective Michael Addition of the 2‐(1‐Ethylpropoxy)acetaldehyde to N ‐[(1 Z )‐2‐Nitroethenyl]acetamide – Optimization of the Key Step in the Organocatalytic Oseltamivir Synthesis

Author(s) -

Hajzer Viktória,

Latika Attila,

Durmis Július,

Šebesta Radovan

Publication year - 2012

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.201200527

Subject(s) - chemistry , michael reaction , enantioselective synthesis , amine gas treating , acetamide , yield (engineering) , combinatorial chemistry , enantiomer , acetaldehyde , organic chemistry , catalysis , stereochemistry , materials science , metallurgy , ethanol

Organocatalytic Michael addition of alkoxyacetaldehyde 1 to N‐protected 2‐nitroethene‐1‐amine 2 ( Scheme 2 ) is a key step in the synthesis of an important antiviral agent, oseltamivir. Screening of a large array of structurally diverse acids as potential promoters led to the identification of several useful acidic additives for this reaction ( Tables 1–4 ). Also other reaction parameters were investigated with the aim of improving the diastereoselectivity of the Michael addition, while maintaining high enantiomer purity and yield ( Tables 5 and 6 ).

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