A Practical Synthetic Approach to Chiral (α-Chloroalkyl)boronic Esters via Iridium-Catalyzed Chemoselective Hydrogenation of Chloro-Substituted Alkenyl Boronates

Autor:	Stephen J. Roseblade, Ulrike Nettekoven, Antonio Zanotti-Gerosa, Ivana Gazic Smilovic, Eva Casas‐Arce, Zdenko Časar
Rok vydání:	2013
Předmět:	Ligand Organic Chemistry Enantioselective synthesis Halogenation chemistry.chemical_element Combinatorial chemistry Catalysis chemistry.chemical_compound chemistry Iridium Chemoselectivity Enantiomeric excess Derivative (chemistry)
Zdroj:	Synthesis. 45:2824-2831
ISSN:	1437-210X 0039-7881
Popis:	Chiral (α-chloroalkyl)boronic esters are obtained by homogeneous asymmetric iridium-catalyzed chemoselective hydrogenation of (1-chloro-1-alkenyl)boronic esters. P,N–Iridium catalysis provides low level of dehalogenation during the hydrogenation, while the catalyst activity and enantioselectivity essentially depends on the applied P,N ligand features. Fine tuning of P,N ligand structures enables high conversions, broad substrate acceptance, and high to excellent enantioselectivities with enantiomeric excess values up to 94% along with low levels of dechlorination. Low catalyst loading with S/C = 200 can also be achieved for the preparation of an industrially important isobutyl derivative.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::422eea5acd50ce036a2a03534f4d0db9 https://doi.org/10.1055/s-0033-1338512 Zobrazit plný text záznamu