Literature DB >> 22497425

Efficient chiral monophosphorus ligands for asymmetric Suzuki-Miyaura coupling reactions.

Wenjun Tang1, Nitinchandra D Patel, Guangqing Xu, Xiaobing Xu, Jolaine Savoie, Shengli Ma, Ming-Hong Hao, Santosh Keshipeddy, Andrew G Capacci, Xudong Wei, Yongda Zhang, Joe J Gao, Wenjie Li, Sonia Rodriguez, Bruce Z Lu, Nathan K Yee, Chris H Senanayake.   

Abstract

A series of novel P-chiral monophosphorus ligands exhibit efficiency in asymmetric Suzuki-Miyaura coupling reactions, enabling the construction of an array of chiral biaryl products in high yields and excellent enantioselectivities (up to 96% ee) under mild conditions. The carbonyl-benzooxazolidinone moiety in these chiral biaryl products allows facile derivatization for further synthetic applications. A computational study has revealed that a π-π interaction between the two coupling partners can enhance the enantioselectivity of the coupling reaction.

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Year:  2012        PMID： 22497425     DOI： 10.1021/ol300659d

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  9 in total

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Authors:  Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal:  Chem Rev       Date:  2015-08-13       Impact factor: 60.622

2.  Development of Chiral Bis-hydrazone Ligands for the Enantioselective Cross-Coupling Reactions of Aryldimethylsilanolates.

Authors:  Scott E Denmark; Wen-Tau T Chang; K N Houk; Peng Liu
Journal:  J Org Chem       Date:  2014-12-10       Impact factor: 4.354

3.  Computationally Assisted Mechanistic Investigation and Development of Pd-Catalyzed Asymmetric Suzuki-Miyaura and Negishi Cross-Coupling Reactions for Tetra-ortho-Substituted Biaryl Synthesis.

Authors:  Nitinchandra Dahyabhai Patel; Joshua D Sieber; Sergei Tcyrulnikov; Bryan J Simmons; Daniel Rivalti; Krishnaja Duvvuri; Yongda Zhang; Donghong A Gao; Keith R Fandrick; Nizar Haddad; Kendricks So Lao; Hari Prasad Reddy Mangunuru; Soumik Biswas; Bo Qu; Nelu Grinberg; Scott Pennino; Heewon Lee; Jinhua J Song; B Frank Gupton; Neil K Garg; Marisa C Kozlowski; Chris H Senanayake
Journal:  ACS Catal       Date:  2018-09-20       Impact factor: 13.084

4.  Pd-catalyzed asymmetric Suzuki-Miyaura coupling reactions for the synthesis of chiral biaryl compounds with a large steric substituent at the 2-position.

Authors:  Yongsu Li; Bendu Pan; Xuefeng He; Wang Xia; Yaqi Zhang; Hao Liang; Chitreddy V Subba Reddy; Rihui Cao; Liqin Qiu
Journal:  Beilstein J Org Chem       Date:  2020-05-11       Impact factor: 2.883

5.  An Enantioselective Suzuki-Miyaura Coupling To Form Axially Chiral Biphenols.

Authors:  Robert Pearce-Higgins; Larissa N Hogenhout; Philip J Docherty; David M Whalley; Padon Chuentragool; Najung Lee; Nelson Y S Lam; Thomas M McGuire; Damien Valette; Robert J Phipps
Journal:  J Am Chem Soc       Date:  2022-08-15       Impact factor: 16.383

6.  Asymmetric Oxidative Coupling of Phenols and Hydroxycarbazoles.

Authors:  Houng Kang; Young Eun Lee; Peddiahgari Vasu Govardhana Reddy; Sangeeta Dey; Scott E Allen; Kyle A Niederer; Paul Sung; Kirsten Hewitt; Carilyn Torruellas; Madison R Herling; Marisa C Kozlowski
Journal:  Org Lett       Date:  2017-10-12       Impact factor: 6.005

7.  An enantioselective artificial Suzukiase based on the biotin-streptavidin technology.

Authors:  Anamitra Chatterjee; Hendrik Mallin; Juliane Klehr; Jaicy Vallapurackal; Aaron D Finke; Laura Vera; May Marsh; Thomas R Ward
Journal:  Chem Sci       Date:  2015-10-19       Impact factor: 9.825

8.  Enantioselective palladium-catalyzed diboration of 1,1-disubstituted allenes.

Authors:  Jiawang Liu; Ming Nie; Qinghai Zhou; Shen Gao; Wenhao Jiang; Lung Wa Chung; Wenjun Tang; Kuiling Ding
Journal:  Chem Sci       Date:  2017-05-16       Impact factor: 9.825

9.  Efficient syntheses of (-)-crinine and (-)-aspidospermidine, and the formal synthesis of (-)-minfiensine by enantioselective intramolecular dearomative cyclization.

Authors:  Kang Du; He Yang; Pan Guo; Liang Feng; Guangqing Xu; Qinghai Zhou; Lung Wa Chung; Wenjun Tang
Journal:  Chem Sci       Date:  2017-07-03       Impact factor: 9.825
  9 in total

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