727416-63-9Relevant academic research and scientific papers
Catalytic asymmetric hydrogenation of indoles using a rhodium complex with a chiral bisphosphine ligand PhTRAP
Kuwano, Ryoichi,Kashiwabara, Manabu,Sato, Koji,Ito, Takashi,Kaneda, Kohei,Ito, Yoshihiko
, p. 521 - 535 (2007/10/03)
Highly enantioselective hydrogenation of N-protected indoles was successfully developed by use of the rhodium catalyst generated in situ from [Rh(nbd)2]SbF6 and the chiral bisphosphine PhTRAP, which can form a trans-chelate complex with a transition metal atom. The PhTRAP-rhodium catalyst required a base (e.g., Cs2CO3) for the achievement of high enantioselectivity. Various 2-substituted N-acetylindoles were converted into the corresponding chiral indolines with up to 95% ee. The hydrogenations of 3-substituted N-tosylindoles yielded indolines possessing a stereogenic center at the 3-position with high enantiomeric excesses (up to 98% ee).
Highly enantioselective synthesis of chiral 3-substituted indolines by catalytic asymmetric hydrogenation of indoles
Kuwano, Ryoichi,Kaneda, Kohei,Ito, Takashi,Sato, Koji,Kurokawa, Takashi,Ito, Yoshihiko
, p. 2213 - 2215 (2007/10/03)
N-Tosyl 3-substituted indoles were hydrogenated with high enantioselectivities (95-98% ee) by use of a trans-chelating chiral bisphosphine, (S,S)-(R,R)-PhTRAP ligand. The chiral catalyst, which was generated in situ from [Rh(nbd)2]SbF6, PhTRAP, and Cs 2CO3, is useful for enantioselectively synthesizing a range of diverse optically active indolines possessing a chiral carbon at the 3-position.
