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An unprecedented synthesis of axially chiral biaryls by rearrangement and aromatization of carbocations with central-to-axial conversion of chirality

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Science China Chemistry 2024年第9期67卷 2998-3003页

作者： Qi Liu Xue-Dong Li Liang Cheng Li Liu Beijing National Laboratory for Molecular Sciences(BNLMS) CAS Key Laboratory of Molecular Recognition and FunctionCAS Research/Education Center for Excellence in Molecular SciencesInstitute of ChemistryChinese Academy of SciencesBeijing 100190China University of Chinese Academy of Sciences Beijing 100049China

The central-to-axial chirality conversion represents a fascinating class of chemical processes consisting of the destruction of stereogenic centers and the simultaneous installation of axial chiral elements,which provides efficient methods for the preparation of axially chiral ***,developing catalytic asymmetric approaches for constructing these central chirality precursors and the efficient central-to-axial chirality conversion remains a challenge due to the requirement of aromatization or elimination *** this work,we have developed an unprecedented enantioselective intramolecular FriedelCrafts alkylation with unactivated-ketone carbonyls from which a chiral tertiary alcohol was generated with high efficiency and excellent *** addition,the central-to-axial chirality conversion strategy has been successfully applied to the synthesis of enantioenriched biaryls via a less-explored carbocation-initiated rearrangement and aromatization under the promotion of Lewis *** methodology provided a straightforward and sustainable access to a broad range of biaryl-2-carboxylic acid and in excellent yields(up to 92%)and excellent central-to-axial chirality conversion(up to 99%conversion percentage).This work could be a great model for developing new methods for synthesizing axially chiral biaryls and a general protocol for the rearrangement and aromatization of carbocations for further functionalization.

关键词： br?nsted acid catalysis desymmetrization phosphoric acid axially chiral biaryls central-to-axial conversion

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Carbene-Catalyzed Asymmetric Ring-Opening Reaction of Biaryl Lactams to Access axially chiral biaryls

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Chinese Journal of Chemistry 2024年第15期42卷 1734-1740页

作者： Guanjie Wang Guowei Yuan Chenlong Wei Ye Zhang Haibin Zhu Weiqi Yang Dongping Shi Xiaoxiang Zhang Zhenqian Fu Institute of Advanced Materials Nanjing Tech UniversityNanjingJiangsu 211816China Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources College of Chemical EngineeringNanjing Forestry UniversityNanjingJiangsu 210037China

axially chiral biaryls represent the most important class of atropisomers,and they widely exist in natural products and biologically active *** also constitute a unique scaffold for chiral ligands and catalysts in organic *** development of synthetic methods to obtain such chiral compounds has received widespread attention,among which catalytically atroposelective ring-opening of configurationally labile compounds represents one of the most attractive *** substrates with strained cyclic structures,such as the renowned Bringmann's lactones,can undergo asymmetric transformation into stable *** advancement primarily relies on metal catalyst combined with well-designed chiral ligands,the approaches utilizing organocatalysis as a critical resolution strategy are notably *** this study,we disclosed a N-heterocyclic carbene(NHC)-catalyzed asymmetric ring-opening reaction of biaryl lactams via direct atroposelective nucleophilic *** optimized bulky carbene catalyst ensures that the reaction can proceed under mild conditions,affording the desired product with good to excellent yields and atroposelectivity.

关键词： N-Heterocyclic carbene axially chiral biaryls Organocatalysis Ring-opening reactions Dibenzo cyclic lactams axially chiral amino acids Amide C-N bond activation Atropisomerism Asymmetric catalysis Lactams

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Merging C–H and C–C Activation in Pd(Ⅱ)-Catalyzed Enantioselective Synthesis of axially chiral biaryls

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CCS Chemistry 2021年第12期3卷 455-465页

作者： Hao-Ming Chen Gang Liao Cheng-Kai Xu Qi-Jun Yao Shuo Zhang Bing-Feng Shi Department of Chemistry Zhejiang UniversityHangzhou 310027 School of Biotechnology and Health Sciences Wuyi UniversityJiangmen 529020

The merging of C-H and C-C bond cleavage into one single chemical process remains a daunting challenge,especially in an asymmetric ***,a Pd(Ⅱ)-catalyzed enantioselective tandem C-H/C-C activation for the synthesis of axially chiral biaryls is *** types of simple cyclopropanes,such as vinylcyclopropanes and cyclopropanols,were used as efficient and readily available coupling partners.

关键词： palladium C–H activation C–C cleavage atroposelectivity axially chiral biaryls

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Catalytic asymmetric Catellani-type reaction: A powerful tool for axial chirality construction

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Green Synthesis and Catalysis 2020年第2期1卷 83-85页

作者： Yue Dong Renshuai Liu Wei Wang Department of Pharmacology and Toxicology Department Chemistry and BiochemistryUniversity of Arizona Cancer CenterBIO5 InstituteUniversity of ArizonaArizona 85721United States

This highlight summarizes a recent development of a catalytic enantioselective Catellani-type reaction for the synthesis of axially chiral *** chirality induction is solely governed by chiral norbornene ligand in the Pd mediated ortho C–H functionalization and ipso cross-coupling *** preparative power of the methodology is demonstrated as a powerful manifold for the divergent synthesis of structurally diverse axially chiral biaryls and chiral fluorenols.

关键词： axially chiral biaryls Asymmetric Catellani reaction C-H functionalization Cross coupling Divergent synthesis

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