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Rhodium‐Catalyzed Enantioselective Intramolecular CH Silylation for the Syntheses of Planar‐Chiral Metallocene Siloles
Author(s) -
Zhang QingWei,
An Kun,
Liu LiChuan,
Yue Yuan,
He Wei
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201502548
Subject(s) - enantioselective synthesis , rhodium , cyclopentadiene , metallocene , chemistry , steric effects , silylation , intramolecular force , reactivity (psychology) , catalysis , organic chemistry , stereochemistry , polymerization , polymer , medicine , alternative medicine , pathology
Reported herein is the rhodium‐catalyzed enantioselective CH bond silylation of the cyclopentadiene rings in Fe and Ru metallocenes. Thus, in the presence of ( S )‐TMS‐Segphos, the reactions took place under very mild conditions to afford metallocene‐fused siloles in good to excellent yields and with ee values of up to 97 %. During this study it was observed that the steric hindrance of chiral ligands had a profound influence on the reactivity and enantioselectivity of the reaction, and might hold the key to accomplishing conventionally challenging asymmetric CH silylations.