期刊
CHEMSUSCHEM
卷 13, 期 14, 页码 3583-3588出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.202001142
关键词
amines; deep eutectic solvents; Grignard reagents; imines; organolithium reagents
资金
- Ministero dell'Universite della Ricerca (MIUR-PRIN) [2017A5HXFC_002]
- Interuniversity Consortium C.I.N.M.P.I.S.
- University of Bari A. Moro [PernaF.18 FondiAteneo15-16, VitaleP.18 FondiAteneo15-16]
- PhosAgro/UNESCO/IUPAC
- Spanish MINECO [CTQ2016-81797-REDC, CTQ2016-75986-P]
Highly polarized organometallic compounds of s-block elements are added smoothly to chiralN-tert-butanesulfinyl imines in the biodegradabled-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).
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