Catalytic Asymmetric Hydrogenation of Indoles Using a Rhodium Complex with a Chiral Bisphosphine Ligand PhTRAP

Autor:	Yoshihiko Ito, Ryoichi Kuwano, Koji Sato, Kohei Kaneda, Manabu Kashiwabara, Takashi Ito
Rok vydání:	2006
Předmět:	Ligand Organic Chemistry Asymmetric hydrogenation Enantioselective synthesis chemistry.chemical_element General Medicine Medicinal chemistry Catalysis Rhodium Stereocenter Inorganic Chemistry chemistry Transition metal Organic chemistry Physical and Theoretical Chemistry Enantiomer
Zdroj:	ChemInform. 37
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200633128
Popis:	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).
Databáze:	OpenAIRE
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