A promising new catalyst family for enantioselective cycloadditions involving allenes and imines: chiral phosphines with transition metal–CH2–P: linkages Academic Article uri icon

abstract

  • The racemic rhenium-containing phosphine (η5-C5H5)Re(NO)(PPh3)(CH2PPh3) (3) catalyzes the [3+2] cycloaddition of H2C{double bond, long}C{double bond, long}CHCO2Et and N-tosyl imines ArCH{double bond, long}NTs in C6H6 (RT, 1 d, 20 mol %) to give 2-aryl-3-carbethoxy-3-pyrrolines (Ar{double bond, long}p-C6H4X (X = H, NO2, OMe, Me, Cl, Br), 2-furyl; 95-84% isolated). Similar reactions with enantiopure (S)-3 are conducted in C6H5Cl at -30 °C (8 d) to maximize enantioselectivities (60-51% ee; 93-90% isolated). © 2006 Elsevier Ltd. All rights reserved.

author list (cited authors)

  • Scherer, A., & Gladysz, J. A.

citation count

  • 73

publication date

  • September 2006