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Asymmetric Hydroboration of Heteroaryl Ketones by Aluminum Catalysis
Author(s) -
Yury Lebedev,
I. E. Polishchuk,
Bholanath Maity,
Miguel Dinis Veloso Guerreiro,
Luigi Cavallo,
Magnus Rueping
Publication year - 2019
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.9b10364
Subject(s) - chemistry , hydroboration , catalysis , organic chemistry , combinatorial chemistry
A series of methyl aluminum complexes bearing chiral biphenol-type ligands were found to be highly active catalysts in the asymmetric reduction of heterocyclic ketones (S/C = 100-500, ee up to 99%). The protocol is suitable for a wide range of substrates and has a high tolerance to functional groups. The formed 2-heterocyclic-alcohols are valuable building blocks in drug discovery or can be used as ligands in asymmetric catalysis. Isolation and comprehensive characterization of the reaction intermediates support a catalysis cycle proposed by DFT calculations.

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