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Easily Accessible and Highly Tunable Bisphosphine Ligands for Asymmetric Hydroformylation of Terminal and Internal Alkenes
Author(s) -
Xu Kun,
Zheng Xin,
Wang Zhiyong,
Zhang Xumu
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201304684
Subject(s) - hydroformylation , steric effects , alkene , ligand (biochemistry) , chemistry , enantioselective synthesis , substrate (aquarium) , enantiomer , stereochemistry , combinatorial chemistry , catalysis , organic chemistry , rhodium , receptor , biology , ecology , biochemistry
An efficient methodology for synthesizing a small library of easily tunable and sterically bulky ligands for asymmetric hydroformylation (AHF) has been reported. Five groups of alkene substrates have been tested with excellent conversions, moderate‐to‐excellent regio‐ and enantioselectivities. Among the best result of the reported literature, application of ligand 1 c in the highly selective AHF of the challenging substrate 2,5‐dihydrofuran yielded almost one isomer in up to 99 % conversion along with enantiomeric excesses ( ee ) of up to 92 %. Highly enantioselective AHF of dihydropyrrole substrates is achieved using the same ligand, with up to 95 % ee and up to >1:50 β‐isomer/α‐isomer ratio.