Literature DB >> 20131819

Asymmetric binary-acid catalysis with chiral phosphoric acid and MgF(2): catalytic enantioselective Friedel-Crafts reactions of beta,gamma-unsaturated alpha-ketoesters.

Jian Lv1, Xin Li, Long Zhong, Sanzhong Luo, Jin-Pei Cheng.   

Abstract

A unique binary chiral phosphoric acid 1a/MgF(2) catalyst that enables effective catalysis of asymmetric Friedel-Crafts reactions of phenols with up to 82% yield and >99% ee is presented. A dramatic synergistic effect has been observed in the combinations of two types of acids, wherein a highly active binary-acid catalyst can be generated from two individually inert acids.

Entities:  

Year:  2010        PMID： 20131819     DOI： 10.1021/ol1000928

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


  10 in total

1.  A Nucleophilic Strategy for Enantioselective Intermolecular α-Amination: Access to Enantioenriched α-Arylamino Ketones.

Authors:  Dillon H Miles; Joan Guasch; F Dean Toste
Journal:  J Am Chem Soc       Date:  2015-06-12       Impact factor: 15.419

2.  Enantioselective Pictet-Spengler Reactions of Isatins for the Synthesis of Spiroindolones.

Authors:  Joseph J Badillo; Abel Silva-García; Benjamin H Shupe; James C Fettinger; Annaliese K Franz
Journal:  Tetrahedron Lett       Date:  2011-10-26       Impact factor: 2.415

3.  Syntheses of (+)-30-epi-, (-)-6-epi-, (±)-6,30-epi-13,14-Didehydroxyisogarcinol and (±)-6,30-epi-Garcimultiflorone A Utilizing Highly Diastereoselective, Lewis Acid-Controlled Cyclizations.

Authors:  Jonathan H Boyce; Vincent Eschenbrenner-Lux; John A Porco
Journal:  J Am Chem Soc       Date:  2016-10-27       Impact factor: 15.419

4.  Chiral magnesium BINOL phosphate-catalyzed phosphination of imines: access to enantioenriched α-amino phosphine oxides.

Authors:  Gajendrasingh K Ingle; Yuxue Liang; Michael G Mormino; Guilong Li; Frank R Fronczek; Jon C Antilla
Journal:  Org Lett       Date:  2011-03-17       Impact factor: 6.005

5.  Catalytic asymmetric aza-Darzens reaction with a vaulted biphenanthrol magnesium phosphate salt.

Authors:  Shawn E Larson; Guilong Li; Gerald B Rowland; Denise Junge; Rongcai Huang; H Lee Woodcock; Jon C Antilla
Journal:  Org Lett       Date:  2011-04-05       Impact factor: 6.005

6.  Methyl 5-hy-droxy-3-phenyl-1,2-oxazolidine-5-carboxyl-ate.

Authors:  Jia Ye; Ya-Nan Liu; Yu Cheng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-04-25

7.  Lithium BINOL phosphate catalyzed desymmetrization of meso-epoxides with aromatic thiols.

Authors:  Gajendrasingh Ingle; Michael G Mormino; Jon C Antilla
Journal:  Org Lett       Date:  2014-10-15       Impact factor: 6.005

8.  Catalytic asymmetric total syntheses of myrtucommuacetalone, myrtucommuacetalone B, and callistrilones A, C, D and E.

Authors:  Min-Jing Cheng; Jia-Qing Cao; Xin-Yi Yang; Li-Ping Zhong; Li-Jun Hu; Xi Lu; Bao-Long Hou; Ya-Jian Hu; Ying Wang; Xue-Fu You; Lei Wang; Wen-Cai Ye; Chuang-Chuang Li
Journal:  Chem Sci       Date:  2017-11-27       Impact factor: 9.825

9.  Synthesis, structure and reactivity of a terminal magnesium fluoride compound, [TpBut,Me]MgF: hydrogen bonding, halogen bonding and C-F bond formation.

Authors:  Michael Rauch; Serge Ruccolo; John Paul Mester; Yi Rong; Gerard Parkin
Journal:  Chem Sci       Date:  2015-11-17       Impact factor: 9.825

10.  Chiral Zn(II)-bisamidine complex as a Lewis-Brønsted combined acid catalyst: application to asymmetric Mukaiyama aldol reactions of α-ketoesters.

Authors:  Ryo Gotoh; Masahiro Yamanaka
Journal:  Molecules       Date:  2012-07-30       Impact factor: 4.411
  10 in total

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