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Preparation of Chiral Contiguous Epoxyaziridines and Their Regioselective Ring‐Opening for Drug Syntheses
Author(s) -
Mao Hui,
Jeong Hyeonsu,
Yang Jieun,
Ha HyunJoon,
Yang Jung Woon
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201706161
Subject(s) - regioselectivity , aziridine , chemistry , epoxide , ring (chemistry) , stereoselectivity , stereochemistry , pyrrolidine , aldehyde , combinatorial chemistry , organic chemistry , catalysis
Synthetically valuable chiral (aziridin‐2‐yl)oxirane‐3‐carbaldehydes bearing three consecutive functional groups including aziridine, epoxide, and aldehyde were prepared from the stereoselective epoxidation of (aziridin‐2‐yl)acrylaldehydes with H 2 O 2 using organocatalyst (2 R )‐ or (2 S )‐[diphenyl(trimethylsilyloxy)methyl]pyrrolidine as organocatalyst. The regioselective ring opening of aziridines and epoxides enabled us to achieve the highly efficient asymmetric synthesis of the antibiotic edeine D fragment 3‐hydroxy‐4,5‐diaminopenatanoic acid, an intermediate for the formal synthesis of non‐proteinogenic amino acid (−)‐galantinic acid, and for potent antifungal agent (+)‐preussin, and the medicinally important framework 3‐hydroxy‐2‐hydroxymethylpyrrolidine.