Sirvent, Ana, Hernández-Ibáñez, Sandra, Yus, Miguel, Foubelo, Francisco
Pyrrolidine and Indolizidine Alkaloids from Chiral N-tert-Butanesulfinyl Imines Derived from 4-Halobutanal
Synthesis. 2021, 53: 1749-1759. https://doi.org/10.1055/s-0037-1610763
URI: http://hdl.handle.net/10045/114689
DOI: 10.1055/s-0037-1610763
ISSN: 0039-7881 (Print)
Abstract: 
An efficient stereocontrolled preparation of 2-substituted pyrrolidines and 5-substituted indolizidin-7-ones, by using chiral N-tert-butanesulfinyl imines derived from 4-halobutanal as starting materials, is detailed. Addition of Grignard reagents and a decarboxylative Mannich­ reaction with β-keto acids involving these chiral imines proceeded with high diastereoselectivity. The synthesis of the pyrrolidinic alkaloids (–)-bgugaine, (+)-villatamine B, (–)-norhygrine, trans-dendrochrysanine, and (–)-ruspolinone demonstrated the utility of this methodology.
Keywords:Chiral sulfinyl imines, Diastereoselective additions, Decarboxylative Mannich reaction, Bgugaine, Villatamine, Norhygrine, Trans-dendrochrysanine, Ruspolinone
Georg Thieme Verlag KG
info:eu-repo/semantics/article