Details

Autor(en) / Beteiligte

• Natori, Yoshihiro
• Kikuchi, Shunsuke
• Kondo, Takahiro
• Saito, Yukako
• Yoshimura, Yuichi
• Takahata, Hiroki

Titel

Asymmetric synthesis of 2,5-disubstituted 3-hydroxypyrrolidines based on stereodivergent intramolecular iridium-catalyzed allylic aminationsElectronic supplementary information (ESI) available. See DOI: 10.1039/c3ob42229a

Erscheinungsjahr

2014-02

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Intramolecular iridium-catalyzed allylic aminations of homochiral ( E )-6- N -nosylaminohept-2-en-1-yl methyl carbonates were investigated. The relative position of the 2,5-substituents of the resulting pyrrolidines was found to be controlled by using both enantiomers ( 4 and 5 ) of the appropriate chiral ligand, demonstrating a simple and highly stereodivergent synthetic protocol. Selected trans - and cis -2,5-disubstituted 3-hydroxypyrrolidines ( 2a and 18a ) were converted to (+)-bulgecinine ( 6 ) and (+)-preussin ( 7 ), respectively. An intramolecular iridium-catalyzed allylic cyclization of ( E )-allyic methyl carbonates by an exchange in both enantiomers of the ( S , S , S )-ligand or the ( R , R , R )-ligand afforded the 2,5- trans / cis pyrrolidine derivatives.