Literature DB >> 25851252

Palladium-Catalyzed Dynamic Kinetic Asymmetric Transformation of Racemic Biaryls: Axial-to-Central Chirality Transfer.

Liu Yang, Huayu Zheng, Lei Luo, Jiang Nan, Jingjing Liu, Yaoyu Wang, Xinjun Luan.   

Abstract

The first dynamic kinetic asymmetric transformation of racemic biaryl substrates on the basis of axial-to-central chirality transfer has been realized. Chiral Pd-NHC complexes were found to catalyze the dynamic kinetic asymmetric spiroannulation of 4-(2-bromoaryl)-naphthalen-1-ols (or 2'-bromo-[1,1'-biphenyl]-4-ols) with internal alkynes, affording a series of enantioenriched spirocyclic products bearing an all-carbon quaternary stereocenter in good yields (up to 95%) with excellent enantioselectivities (up to 97% ee).

Entities:  

Year:  2015        PMID: 25851252     DOI: 10.1021/jacs.5b01285

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  10 in total

1.  Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations.

Authors:  Vikram Bhat; Eric R Welin; Xuelei Guo; Brian M Stoltz
Journal:  Chem Rev       Date:  2017-02-06       Impact factor: 60.622

2.  Activation of allylic esters in an intramolecular vinylogous kinetic resolution reaction with synergistic magnesium catalysts.

Authors:  Dan Li; Yuling Yang; Minmin Zhang; Linqing Wang; Yingfan Xu; Dongxu Yang; Rui Wang
Journal:  Nat Commun       Date:  2020-05-22       Impact factor: 14.919

3.  Chiral phosphoric acid catalyzed aminative dearomatization of α-naphthols/Michael addition sequence.

Authors:  Zi-Lei Xia; Chao Zheng; Ren-Qi Xu; Shu-Li You
Journal:  Nat Commun       Date:  2019-07-17       Impact factor: 14.919

4.  Electrooxidative palladium- and enantioselective rhodium-catalyzed [3 + 2] spiroannulations.

Authors:  Wen Wei; Alexej Scheremetjew; Lutz Ackermann
Journal:  Chem Sci       Date:  2022-02-10       Impact factor: 9.825

5.  Synthesis of tetracyclic indolin-3-ones through Pd-catalyzed intramolecular deacetylative dearomatization of 3-acetoxy-indoles.

Authors:  Ren-Xiao Liang; Ke Wang; Ling-Jie Song; Wei-Jian Sheng; Yi-Xia Jia
Journal:  RSC Adv       Date:  2019-05-07       Impact factor: 3.361

6.  Divergent synthesis of benzazepines and bridged polycycloalkanones via dearomative rearrangement.

Authors:  Qiu Shi; Zhehui Liao; Zhili Liu; Jiajia Wen; Chenguang Li; Jiamin He; Jiazhen Deng; Shan Cen; Tongxiang Cao; Jinming Zhou; Shifa Zhu
Journal:  Nat Commun       Date:  2022-07-29       Impact factor: 17.694

7.  Formal (4+1)-Cyclization of Ammonium Ylides with Vinylogous para-Quinone Methides.

Authors:  Lukas Roiser; Katharina Zielke; Mario Waser
Journal:  Synthesis (Stuttg)       Date:  2018-09-05       Impact factor: 3.157

8.  Two-in-one strategy for fluorene-based spirocycles via Pd(0)-catalyzed spiroannulation of o-iodobiaryls with bromonaphthols.

Authors:  Bojun Tan; Long Liu; Huayu Zheng; Tianyi Cheng; Dianhu Zhu; Xiaofeng Yang; Xinjun Luan
Journal:  Chem Sci       Date:  2020-09-08       Impact factor: 9.825

9.  Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives.

Authors:  Yu Zhang; Yuting Liao; Xiaohua Liu; Xi Xu; Lili Lin; Xiaoming Feng
Journal:  Chem Sci       Date:  2017-07-24       Impact factor: 9.825

10.  Construction of spirocarbocycles via gold-catalyzed intramolecular dearomatization of naphthols.

Authors:  Wen-Ting Wu; Ren-Qi Xu; Liming Zhang; Shu-Li You
Journal:  Chem Sci       Date:  2016-02-02       Impact factor: 9.825

  10 in total

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