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trans ‐Cyclooctenes as Chiral Ligands in Rhodium‐Catalyzed Asymmetric 1,4‐Additions
Author(s) -
Nagano Tagui,
Einaru Shunsuke,
Shitamichi Kenta,
Asano Keisuke,
Matsubara Seijiro
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000956
Subject(s) - chemistry , rhodium , substituent , enantioselective synthesis , catalysis , cyclooctene , allylic rearrangement , asymmetric induction , combinatorial chemistry , asymmetric hydrogenation , reagent , stereochemistry , medicinal chemistry , organic chemistry
trans ‐Cyclooctenes serve as asymmetric ligands for the rhodium‐catalyzed 1,4‐additions of organotin reagents to enones. We demonstrate, for the first time, that these chiral olefins can provide efficient coordination spheres for asymmetric metal catalysis. As the asymmetric environment around the reaction site is constructed by the trans ‐cyclooctene framework, the introduction of a substituent at the allylic position further improves enantioselectivity to 93 % ee . These findings provide new chiral framework designs for the asymmetric ligands of metal catalysts.