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

A 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.

Bibliographic Details

Main Authors:	Pérez, Sixto J., Purino, Martín, Cruz, Daniel A., López-Soria, Juan M., Carballo, Rubén M., Ramírez, Miguel A., Fernández, Israel, Martín, Víctor S., Padrón, Juan I.
Other Authors:	Ministerio de Economía y Competitividad (España)
Format:	artículo biblioteca
Published:	Wiley-VCH 2016-10-17
Subjects:	Nitrogen heterocycles, Alkaloids, Iron, Hydroamination, Cyclization,
Online Access:	http://hdl.handle.net/10261/183956 http://dx.doi.org/10.13039/100012000 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100003329
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