Literature DB >> 23488914

Pd-catalyzed asymmetric β-hydride elimination en route to chiral allenes.

Ian T Crouch1, Robynne K Neff, Doug E Frantz.   

Abstract

We wish to report our preliminary results on the discovery and development of a catalytic, asymmetric β-hydride elimination from vinyl Pd(II)-complexes derived from enol triflates to access chiral allenes. To achieve this, we developed a class of chiral phosphite ligands that demonstrate high enantioselectivity, allow access of either allene enantiomer, and are readily synthesized. The methodology is demonstrated on over 20 substrates, and application to the formal asymmetric total synthesis of the natural product, (+)-epibatidine, is also provided.

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Year:  2013        PMID: 23488914      PMCID: PMC3758424          DOI: 10.1021/ja401606e

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


  29 in total

1.  Synthesis of (-)-epibatidine.

Authors:  D A Evans; K A Scheidt; C W Downey
Journal:  Org Lett       Date:  2001-09-20       Impact factor: 6.005

Review 2.  Allenes in catalytic asymmetric synthesis and natural product syntheses.

Authors:  Shichao Yu; Shengming Ma
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-23       Impact factor: 15.336

3.  Gram-scale synthesis of (-)-epibatidine.

Authors:  Chi-Lik Ken Lee; Teck-Peng Loh
Journal:  Org Lett       Date:  2005-07-07       Impact factor: 6.005

4.  Synchronized aromaticity as an enthalpic driving force for the aromatic Cope rearrangement.

Authors:  David J Babinski; Xiaoguang Bao; Marie El Arba; Bo Chen; David A Hrovat; Weston Thatcher Borden; Doug E Frantz
Journal:  J Am Chem Soc       Date:  2012-09-18       Impact factor: 15.419

5.  Palladium-catalyzed elimination/isomerization of enol triflates into 1,3-dienes.

Authors:  Ian T Crouch; Timothy Dreier; Doug E Frantz
Journal:  Angew Chem Int Ed Engl       Date:  2011-05-13       Impact factor: 15.336

6.  Dynamic kinetic asymmetric allylic alkylations of allenes.

Authors:  Barry M Trost; Daniel R Fandrick; Diana C Dinh
Journal:  J Am Chem Soc       Date:  2005-10-19       Impact factor: 15.419

7.  Synthesis of substituted pyrazoles via tandem cross-coupling/electrocyclization of enol triflates and diazoacetates.

Authors:  David J Babinski; Hector R Aguilar; Raymond Still; Doug E Frantz
Journal:  J Org Chem       Date:  2011-06-27       Impact factor: 4.354

8.  How easy are the syntheses of allenes?

Authors:  Shichao Yu; Shengming Ma
Journal:  Chem Commun (Camb)       Date:  2011-03-15       Impact factor: 6.222

9.  Stereoselective synthesis of acetoacetate-derived enol triflates.

Authors:  David Babinski; Omid Soltani; Doug E Frantz
Journal:  Org Lett       Date:  2008-06-10       Impact factor: 6.005

Review 10.  Synthesis and properties of allenic natural products and pharmaceuticals.

Authors:  Anja Hoffmann-Röder; Norbert Krause
Journal:  Angew Chem Int Ed Engl       Date:  2004-02-27       Impact factor: 15.336

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  17 in total

1.  Asymmetric oxidative dearomatizations promoted by hypervalent iodine(III) reagents: an opportunity for rational catalyst design?

Authors:  Andrew M Harned
Journal:  Tetrahedron Lett       Date:  2014-08-20       Impact factor: 2.415

2.  Formation of Chiral Allylic Ethers via an Enantioselective Palladium-Catalyzed Alkenylation of Acyclic Enol Ethers.

Authors:  Harshkumar H Patel; Matthew B Prater; Scott O Squire; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2018-04-27       Impact factor: 15.419

3.  Intramolecular Chirality Transfer [2 + 2] Cycloadditions of Allenoates and Alkenes.

Authors:  Yao Xu; Young J Hong; Dean J Tantillo; M Kevin Brown
Journal:  Org Lett       Date:  2017-07-07       Impact factor: 6.005

4.  Enantioselective Synthesis of Allenes by Catalytic Traceless Petasis Reactions.

Authors:  Yao Jiang; Abdallah B Diagne; Regan J Thomson; Scott E Schaus
Journal:  J Am Chem Soc       Date:  2017-01-25       Impact factor: 15.419

5.  Chiral Allenylcarbonyls - Underexploited Building Blocks for Complex Synthesis.

Authors:  Krishna Yadavalli; Salvatore D Lepore
Journal:  Lett Org Chem       Date:  2022-02-01       Impact factor: 0.797

6.  Iron-Catalyzed Contrasteric Functionalization of Allenic C(sp2)-H Bonds: Synthesis of α-Aminoalkyl 1,1-Disubstituted Allenes.

Authors:  Yidong Wang; Sarah G Scrivener; Xiao-Dong Zuo; Ruihan Wang; Philip N Palermo; Ethan Murphy; Austin C Durham; Yi-Ming Wang
Journal:  J Am Chem Soc       Date:  2021-09-07       Impact factor: 16.383

7.  Generation of Axially Chiral Fluoroallenes through a Copper-Catalyzed Enantioselective β-Fluoride Elimination.

Authors:  Thomas J O'Connor; Binh Khanh Mai; Jordan Nafie; Peng Liu; F Dean Toste
Journal:  J Am Chem Soc       Date:  2021-08-16       Impact factor: 16.383

8.  Palladium-catalyzed chemoselective allylic substitution, Suzuki-Miyaura cross-coupling, and allene formation of bifunctional 2-B(pin)-substituted allylic acetate derivatives.

Authors:  Byeong-Seon Kim; Mahmud M Hussain; Nusrah Hussain; Patrick J Walsh
Journal:  Chemistry       Date:  2014-07-30       Impact factor: 5.236

9.  Catalytic asymmetric and stereodivergent oligonucleotide synthesis.

Authors:  Aaron L Featherston; Yongseok Kwon; Matthew M Pompeo; Oliver D Engl; David K Leahy; Scott J Miller
Journal:  Science       Date:  2021-02-12       Impact factor: 47.728

10.  Synthesis of highly functionalized tri- and tetrasubstituted alkenes via Pd-catalyzed 1,2-hydrovinylation of terminal 1,3-dienes.

Authors:  Vaneet Saini; Mark O'Dair; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2015-01-06       Impact factor: 15.419

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