Catalytic Enantioselective Intramolecular C(sp3)−H Amination of 2‐Azidoacetamides

• Published in: Angewandte Chemie International Edition Vol. 58; no. 4; pp. 1088 - 1093
• Main Authors: Zhou, Zijun, Chen, Shuming, Qin, Jie, Nie, Xin, Zheng, Xingwen, Harms, Klaus, Riedel, Radostan, Houk, K. N., Meggers, Eric
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 21.01.2019; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Aliphatic compounds; Amination; asymmetric catalysis; azides; Catalysis; Catalysts; Chemistry; Chemistry, Multidisciplinary; chiral-at-metal complexes; Coordination compounds; Enantiomers; Physical Sciences; Ruthenium; ruthenium catalysis; Ruthenium compounds; Science & Technology; Substrates; IMIDO COMPLEXES; CYTOCHROME-P450; IRIDIUM; BOND AMINATION; AMIDATION; asymmetric catalysis; ruthenium catalysis; azides; chiral-at-metal complexes; AZIRIDINATION; CHEMISTRY; amination; DERIVATIVES; C-H AMINATION; ALKYL AZIDES

An enantioselective ring‐closing C(sp3)−H amination of 2‐azidoacetamides is catalyzed by a chiral‐at‐metal ruthenium complex and provides chiral imidazolidin‐4‐ones in 31–95 % yield, with enantioselectivities of up to 95 % ee, and at catalyst loadings down to 0.1 mol % (turnover number (TON)=740). T...