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An Easy Access to 1-Azaspiropentane-2-carboxamides – The First Derivatives of a New Type of Amino Acids

✍ Scribed by Markus Tamm; Michael Thutewohl; Carsten B. Ricker; M. Teresa Bes; Armin de Meĳere

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 212 KB
Volume: 1999
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(199909)1999:9<2017::aid-ejoc2017>3.0.co;2-0

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✦ Synopsis

Azaspiropentanecarboxamides 10 and 12 are formed with good (27-59%, 12-48%), while the corresponding esters 9 could only be obtained in poor yields (4-14%). The new αremarkable ease in two steps in a one-pot operation from methyl 2-chloro-2-cyclopropylideneacetate (4) by addition of amino acid amides are surprisingly stable, and they can be incorporated into small peptides as demonstrated with the a primary amine in tetrahydrofuran and subsequent treatment with sodium hydride/triethylamine in the presence preparation of the glycine 13e and the spirocyclopropaneoxazoline derivative 14e. of another equivalent of a primary amine or ammonia. Achievable yields of the amides 10, 12 were moderate to more reactive than simple aziridines due to the spiro-linked [ ] Part 50:

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