Literature DB >> 30451496

Enantioselective Coupling of Dienes and Phosphine Oxides.

Shao-Zhen Nie1,2, Ryan T Davison1, Vy M Dong1.   

Abstract

We report a Pd-catalyzed intermolecular hydrophosphinylation of 1,3-dienes to afford chiral allylic phosphine oxides. Commodity dienes and air stable phosphine oxides couple to generate organophosphorus building blocks with high enantio- and regiocontrol. This method constitutes the first asymmetric hydrophosphinylation of dienes.

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Year:  2018        PMID： 30451496      PMCID： PMC6607437          DOI： 10.1021/jacs.8b11150

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


  40 in total

1.  Palladium-catalyzed hydroamination of 1,3-dienes: a colorimetric assay and enantioselective additions.

Authors:  O Löber; M Kawatsura; J F Hartwig
Journal:  J Am Chem Soc       Date:  2001-05-09       Impact factor: 15.419

2.  Organocatalytic asymmetric hydrophosphination of alpha,beta-unsaturated aldehydes.

Authors:  Armando Carlone; Giuseppe Bartoli; Marcella Bosco; Letizia Sambri; Paolo Melchiorre
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  The atom economy--a search for synthetic efficiency.

Authors:  B M Trost
Journal:  Science       Date:  1991-12-06       Impact factor: 47.728

4.  Intermolecular Hydroamination of 1,3-Dienes To Generate Homoallylic Amines.

Authors:  Xiao-Hui Yang; Alexander Lu; Vy M Dong
Journal:  J Am Chem Soc       Date:  2017-09-27       Impact factor: 15.419

5.  Highly Regio- and Enantioselective Copper-Catalyzed Reductive Hydroxymethylation of Styrenes and 1,3-Dienes with CO2.

Authors:  Yong-Yuan Gui; Naifu Hu; Xiao-Wang Chen; Li Li Liao; Tao Ju; Jian-Heng Ye; Zhen Zhang; Jing Li; Da-Gang Yu
Journal:  J Am Chem Soc       Date:  2017-11-10       Impact factor: 15.419

6.  Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles.

Authors:  Nathan J Adamson; Katherine C E Wilbur; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2018-02-20       Impact factor: 15.419

7.  Palladium-catalyzed reactions of hypophosphorous compounds with allenes, dienes, and allylic electrophiles: methodology for the synthesis of allylic h-phosphinates.

Authors:  Karla Bravo-Altamirano; Isabelle Abrunhosa-Thomas; Jean-Luc Montchamp
Journal:  J Org Chem       Date:  2008-02-15       Impact factor: 4.354

8.  Selective [1,4]-Hydrovinylation of 1,3-Dienes with Unactivated Olefins Enabled by Iron Diimine Catalysts.

Authors:  Valerie A Schmidt; C Rose Kennedy; Máté J Bezdek; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2018-02-21       Impact factor: 15.419

9.  A core metabolic enzyme mediates resistance to phosphine gas.

Authors:  David I Schlipalius; Nicholas Valmas; Andrew G Tuck; Rajeswaran Jagadeesan; Li Ma; Ramandeep Kaur; Anita Goldinger; Cameron Anderson; Jujiao Kuang; Steven Zuryn; Yosep S Mau; Qiang Cheng; Patrick J Collins; Manoj K Nayak; Horst Joachim Schirra; Massimo A Hilliard; Paul R Ebert
Journal:  Science       Date:  2012-11-09       Impact factor: 47.728

10.  Mechanisms of phosphine toxicity.

Authors:  Nisa S Nath; Ishita Bhattacharya; Andrew G Tuck; David I Schlipalius; Paul R Ebert
Journal:  J Toxicol       Date:  2011-04-28
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  11 in total

Review 1.  Recent Progress in the Selective Functionalization of P(O)-OH Bonds.

Authors:  Biquan Xiong; Shipan Xu; Yu Liu; Ke-Wen Tang; Peng-Cheng Qian; Wai-Yeung Wong
Journal:  Top Curr Chem (Cham)       Date:  2021-01-11

2.  Enantio- and Diastereoselective Synthesis of Homoallylic α-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes.

Authors:  Chibueze I Onyeagusi; Xinxin Shao; Steven J Malcolmson
Journal:  Org Lett       Date:  2020-02-04       Impact factor: 6.005

3.  Pyridine(diimine) Iron Diene Complexes Relevant to Catalytic [2+2]-Cycloaddition Reactions.

Authors:  C Rose Kennedy; Hongyu Zhong; Matthew V Joannou; Paul J Chirik
Journal:  Adv Synth Catal       Date:  2019-11-19       Impact factor: 5.837

4.  Heteroarene Phosphinylalkylation via a Catalytic, Polarity-Reversing Radical Cascade.

Authors:  J Quentin Buquoi; Jeremy M Lear; Xin Gu; David A Nagib
Journal:  ACS Catal       Date:  2019-05-06       Impact factor: 13.084

5.  α-Silicon effect assisted Curtin-Hammett allylation using allylcopper reagents derived from 1,3-dienylsilanes.

Authors:  Shang Gao; Ming Chen
Journal:  Chem Sci       Date:  2019-06-28       Impact factor: 9.825

6.  Brønsted acid and Pd-PHOX dual-catalysed enantioselective addition of activated C-pronucleophiles to internal dienes.

Authors:  Sangjune Park; Nathan J Adamson; Steven J Malcolmson
Journal:  Chem Sci       Date:  2019-04-17       Impact factor: 9.825

7.  Nickel/Brønsted acid dual-catalyzed regio- and enantioselective hydrophosphinylation of 1,3-dienes: access to chiral allylic phosphine oxides.

Authors:  Jiao Long; Yuqiang Li; Weining Zhao; Guoyin Yin
Journal:  Chem Sci       Date:  2021-12-28       Impact factor: 9.825

8.  Ni-catalyzed asymmetric hydrophosphinylation of conjugated enynes and mechanistic studies.

Authors:  Ya-Qian Zhang; Xue-Yu Han; Yue Wu; Peng-Jia Qi; Qing Zhang; Qing-Wei Zhang
Journal:  Chem Sci       Date:  2022-03-10       Impact factor: 9.825

9.  Synergistic Pd/Cu-catalyzed enantioselective Csp2-F bond alkylation of fluoro-1,3-dienes with aldimine esters.

Authors:  Huimin Yu; Qinglong Zhang; Weiwei Zi
Journal:  Nat Commun       Date:  2022-05-05       Impact factor: 17.694

10.  Enantioselective Addition of Pyrazoles to Dienes*.

Authors:  Alexander Y Jiu; Hannah S Slocumb; Charles S Yeung; Xiao-Hui Yang; Vy M Dong
Journal:  Angew Chem Int Ed Engl       Date:  2021-08-01       Impact factor: 16.823
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