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SELECTED APPLICATIONS OF N-PROTECTED (S)-2-(DIAZOACETYL)PYRROLIDINES

Paulina Pipiak, Grzegorz Mloston
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Abstract


In recent years, the N-protected (S)-2-(diazoacetyl)pyrrolidines have been widely explored as easily available, chiral building blocks bearing the reactive diazo function and have found numerous applications for the multistep synthesis of more complicated heterocycles including some natural products and their analogs. Three types of key reactions performed with N-protected (S)-2-(diazoacetyl)pyrrolidines are a) halogenation via treatment with HX agents and N2 elimination, b) catalytic decomposition and generation of reactive ketenes via the Wolff rearrangement of the intermediate α-oxo carbenes, and c) (3+2) cycloaddition reactions of the diazo 1,3-dipole with C=S dipolarophiles. In this article, mainly the papers from the period after 2001 are reviewed.

How to Cite
Pipiak, P.; Mlostoń, G. Chem. Heterocycl. Compd. 2016, 52, 146. [Khim. Geterotsikl. Soedin. 2016, 52, 146.]

For this article in the English edition see DOI 10.1007/s10593-016-1848-0


Keywords


nitrogen heterocycles; N-protected (S)-proline; (S)-homoproline; diazo compounds; Arndt–Eistert reaction; Wolff rearrangement

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