Premium
Addition of Highly Polarized Organometallic Compounds to N‐tert ‐Butanesulfinyl Imines in Deep Eutectic Solvents under Air: Preparation of Chiral Amines of Pharmaceutical Interest
Author(s) -
Cicco Luciana,
Salomone Antonio,
Vitale Paola,
RíosLombardía Nicolás,
GonzálezSabín Javier,
GarcíaÁlvarez Joaquín,
Perna Filippo M.,
Capriati Vito
Publication year - 2020
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.202001142
Subject(s) - chemistry , eutectic system , substrate (aquarium) , choline chloride , amine gas treating , group 2 organometallic chemistry , combinatorial chemistry , supercritical fluid , organic chemistry , alloy , molecule , oceanography , geology
Highly polarized organometallic compounds of s‐block elements are added smoothly to chiral N‐tert ‐butanesulfinyl imines in the biodegradable d ‐sorbitol/choline chloride eutectic mixture, thereby granting access to enantioenriched primary amines after quantitatively removing the sulfinyl group. The practicality of the method is further highlighted by proceeding at ambient temperature and under air, with very short reaction times (2 min), enabling the preparation of diastereoisomeric sulfinamides in very good yields (74–98 %) and with a broad substrate scope, and the possibility of scaling up the process. The method is demonstrated in the asymmetric syntheses of both the chiral amine side‐chain of ( R , R )‐Formoterol (96 % ee ) and the pharmaceutically relevant ( R )‐Cinacalcet (98 % ee ).