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Hong-Cheng Shen,Ze-Shu Wang,Adam Noble et al. Hong-Cheng Shen et al.
The method shows broad substrate scope, enabling primary, secondary, and even tertiary boronic esters to be employed, and can be used to prepare any of the four possible stereoisomers of a coupled product with vicinal chiral centers.
Markus Tost,Uli Kazmaier Markus Tost
Homologation with substituted carbenoids followed by reaction with carbon nucleophiles resulted in configurationally inverted products and tertiary boronic esters in a highly stereoselective fashion. This approach significantly expands the potential of the Matteson reaction.
Hao Liang,James P Morken Hao Liang
Activation of enantiomerically enriched tertiary alkylboronic esters with adamantyllithium generated in situ enables stereoretentive boron-to-copper transmetalation. The resulting alkylcopper species can undergo cross-coupling reactions wit...
Xuntong Zhang,Chenpeng Gao,James P Morken Xuntong Zhang
Synthesis of stereodefined carbocyclic and heterocyclic tertiary boronic esters is accomplished by performing a conjunctive cross-coupling reaction on preformed cyclic boron ate complexes.
Bingbing Wang,Pan Peng,Wan Ma et al. Bingbing Wang et al.
This process provides an efficient and practical access to primary, secondary, and tertiary boronic esters at a high current.
James D Grayson,Francesca M Dennis,Craig C Robertson et al. James D Grayson et al.
Both secondary and tertiary boronic esters can be used as coupling partners, with mono-alkylation of the aniline occurring selectively. This is a rare example of a transition-metal-mediated transformation of a tertiary alkylboron reagent.
Tao-Tao Gao,Hou-Xiang Lu,Peng-Chao Gao et al. Tao-Tao Gao et al.
Chiral tertiary boronic esters are important precursors to bioactive compounds and versatile synthetic intermediates to molecules containing quaternary stereocenters....Here we show the catalytic asymmetric synthesis of enantioenriched tertiary boronic esters through hydroboration of β,β-disubstituted α,β-unsaturated amides. The Rh-catalyzed hydroboration occurs with previously unattainable selectivity to provide tertiary boronic esters in high enantioselectivity.
Colton R Davis,Irungu K Luvaga,Joseph M Ready Colton R Davis
The three-component coupling provides tertiary boronic esters that can undergo multiple additional functionalizations. An extension to trisubstituted olefins sets three contiguous stereocenters.
Emma K Edelstein,Andrea C Grote,Maximilian D Palkowitz et al. Emma K Edelstein et al.
In addition to being stereospecific, this process also enables the direct amination of tertiary boronic esters in an efficient fashion.
Qingqing Qi,Xuena Yang,Xiaoping Fu et al. Qingqing Qi et al.
This reaction has a broad scope, enabling the synthesis of various α-amino tertiary boronic esters in excellent yields and, importantly, with universally excellent enantiospecificity (>99 % es) and complete retention of configuration.
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