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Copper(I)‐Catalyzed Enantioselective Nucleophilic Borylation of Aliphatic Ketones: Synthesis of Enantioenriched Chiral Tertiary α‐Hydroxyboronates
Author(s) -
Kubota Koji,
Osaki Shun,
Jin Mingoo,
Ito Hajime
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201702826
Subject(s) - enantioselective synthesis , borylation , chemistry , nucleophile , catalysis , carbene , stereospecificity , organic chemistry , combinatorial chemistry , aryl , alkyl
A new method was developed for the first catalytic enantioselective borylation of aliphatic ketones. A variety of substrates reacted efficiently with bis(pinacolato)diboron in the presence of a copper(I)/chiral N‐heterocyclic carbene complex catalyst to furnish optically active tertiary α‐hydroxyboronates with moderate to high enantioselectivities (up to 94 % ee ). Notably, the product could be converted into the chiral tertiary alcohol derivative using a stereospecific boron functionalization process. The theoretical study of the mechanism for the enantioselectivity is also described.