title: Synthesis of (S)-7-amino-5-azaspiro[2.4]heptane via highly enantioselective hydrogenation of protected ethyl 1-(2-aminoaceto)cyclopropanecarboxylates.
abstract: Highly effective asymmetric hydrogenation of protected ethyl 1-(2-aminoaceto)cyclopropane carboxylates in the presence of [RuCl(benzene)(S)-SunPhos]Cl was realized, and high enantioselectivities (up to 98.7% ee) were obtained. This asymmetric hydrogenation provides a key intermediate for the enantioselective synthesis of (S)-7-amino-5-azaspiro[2.4]heptane moiety of quinolone antibacterial agents.
authors.affiliation: School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China.
authors.forename: Ying
authors.initials: Y
authors.lastname: Yao
authors.forename: Weizheng
authors.initials: W
authors.lastname: Fan
authors.forename: Wanfang
authors.initials: W
authors.lastname: Li
authors.forename: Xin
authors.initials: X
authors.lastname: Ma
authors.forename: Lvfeng
authors.initials: L
authors.lastname: Zhu
authors.forename: Xiaomin
authors.initials: X
authors.lastname: Xie
authors.forename: Zhaoguo
authors.initials: Z
authors.lastname: Zhang
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D001372:Aza Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D003521:Cyclopropanes / Q000737:chemistry; D005998:Glycine / Q000737:chemistry; D006536:Heptanes / Q000138:chemical synthesis*; D006865:Hydrogenation; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry; D015363:Quinolones / Q000138:chemical synthesis*; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000900:Anti-Bacterial Agents; D001372:Aza Compounds; D003521:Cyclopropanes; D006536:Heptanes; D010720:Phosphines; D015363:Quinolones; C015766:cyclopropanecarboxylic acid; D012428:Ruthenium; D005998:Glycine