Asymmetric aza-Mannich reactions of sulfinimines: scope and application to the total synthesis of a bromopyrrole alkaloid.
[reaction: see text] An asymmetric intermolecular aza variant of the Mannich reaction is reported utilizing chiral sulfinimine anions as the nucleophile and N-sulfonyl aldimines as the electrophilic component. A wide range of nucleophiles and electrophiles are tolerated by the reaction conditions, delivering the condensation products in good to excellent yield with a high degree of stereocontrol. Application of this methodology to the total synthesis of a natural product is reported.
Lanter
James C
JC
Department of Medicinal Chemisty, Johnson & Johnson Pharmaceutical Research and Development, 1000 Route 202S, Raritan, New Jersey 08869, USA. jlanter@prdus.jnj.com
Chen
Hongfeng
H
Zhang
Xuqing
X
Sui
Zhihua
Z
D000470:Alkaloids / Q000138:chemical synthesis*; D001372:Aza Compounds / Q000737:chemistry*; D002384:Catalysis; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis*; D007097:Imines / Q000737:chemistry*; D008386:Marine Biology; D015394:Molecular Structure; D011743:Pyrimidines / Q000138:chemical synthesis*; D011758:Pyrroles / Q000138:chemical synthesis*; D013441:Sulfinic Acids / Q000737:chemistry*
D000470:Alkaloids; D001372:Aza Compounds; D006842:Hydrocarbons, Brominated; D007097:Imines; D011743:Pyrimidines; D011758:Pyrroles; D013441:Sulfinic Acids; C470326:manzacidin C