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Title

Enantiodivergent Synthesis of (+)- and (-)-Pyrrolidine 197B: Synthesis of trans-2,5-Disubstituted Pyrrolidines by Intramolecular Hydroamination

AuthorsPérez, Sixto J.; Purino, Martín; Cruz, Daniel A.; López-Soria, Juan M.; Carballo, Ruben M.; Ramírez, Miguel A.; Fernández, Israel; Martín, Víctor S.; Padrón, Juan I. CSIC ORCID
KeywordsNitrogen heterocycles
Alkaloids
Iron
Hydroamination
Cyclization
Issue Date17-Oct-2016
PublisherWiley-VCH
CitationChemistry - A European Journal 22(43): 15529-15535 (2016)
AbstractA highly efficient, diastereoselective, iron(III)‐catalyzed intramolecular hydroamination/cyclization reaction involving α‐substituted amino alkenes is described. Thus, enantiopure trans‐2,5‐disubstituted pyrrolidines and trans‐5‐substituted proline derivatives were synthesized by means of a combination of enantiopure starting materials, easily available from l‐α‐amino acids, with sustainable metal catalysts such as iron(III) salts. The scope of this methodology is highlighted in an enantiodivergent approach to the synthesis of both (+)‐ and (−)‐pyrrolidine 197B alkaloids from l‐glutamic acid. In addition, a computational study was carried out to gain insight into the complete diastereoselectivity of the transformation.
Publisher version (URL)https://doi.org/10.1002/chem.201602708
URIhttp://hdl.handle.net/10261/183956
DOIhttp://dx.doi.org/10.1002/chem.201602708
ISSN0947-6539
E-ISSN1521-3765
Appears in Collections:(IPNA) Artículos
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