TY - JOUR AU - Sirvent, Ana; Hernández-Ibáñez, Sandra; Yus, Miguel; Foubelo, Francisco TI - Pyrrolidine and Indolizidine Alkaloids from Chiral N-tert-Butanesulfinyl Imines Derived from 4-Halobutanal SN - 0039-7881 SN - 1437-210X PY - 2021 JO - Synthesis JF - Synthesis LA - EN VL - 53 IS - 10 SP - 1749 EP - 1759 DA - 2021/02/10 KW - chiral sulfinyl imines KW - diastereoselective additions KW - decarboxylative Mannich reaction KW - bgugaine KW - villatamine KW - norhygrine KW - trans-dendrochrysanine KW - ruspolinone AB - 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. PB - Georg Thieme Verlag KG DO - 10.1055/s-0037-1610763 UR - http://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0037-1610763 ER -