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Literature DB >> 21972824

Chiral allene-containing phosphines in asymmetric catalysis.

Feng Cai¹, Xiaotao Pu, Xiangbing Qi, Vincent Lynch, Akella Radha, Joseph M Ready.

Abstract

We demonstrate that allenes, chiral 1,2-dienes, appended with basic functionality can serve as ligands for transition metals. We describe an allene-containing bisphosphine that, when coordinated to Rh(I), promotes the asymmetric addition of arylboronic acids to α-keto esters with high enantioselectivity. Solution and solid-state structural analysis reveals that one olefin of the allene can coordinate to transition metals, generating bi- and tridentate ligands.

Entities: Chemical Disease

Mesh：

Substances：

Year: 2011 PMID： 21972824 PMCID： PMC3216402 DOI： 10.1021/ja207748r

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

18 in total

1. Chiral phosphine-olefin ligands in the rhodium-catalyzed asymmetric 1,4-addition reactions.

Authors: Wei-Liang Duan; Hiroshi Iwamura; Ryo Shintani; Tamio Hayashi
Journal: J Am Chem Soc Date: 2007-01-24 Impact factor: 15.419

2. Rationale behind the resistance of dialkylbiaryl phosphines toward oxidation by molecular oxygen.

Authors: Timothy E Barder; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2007-03-28 Impact factor: 15.419

3. Gold(I)-catalyzed dynamic kinetic enantioselective intramolecular hydroamination of allenes.

Authors: Zhibin Zhang; Christopher F Bender; Ross A Widenhoefer
Journal: J Am Chem Soc Date: 2007-10-30 Impact factor: 15.419

4. The role of bent acyclic allene gold complexes in axis-to-center chirality transfers.

Authors: Vincent Gandon; Gilles Lemière; Alexandra Hours; Louis Fensterbank; Max Malacria
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

5. Enantioselective rhodium-catalyzed addition of arylboronic acids to alpha-ketoesters.

Authors: Hai-Feng Duan; Jian-Hua Xie; Xiang-Chen Qiao; Li-Xin Wang; Qi-Lin Zhou
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

Review 6. Phosphoramidites: marvellous ligands in catalytic asymmetric conjugate addition.

Authors: B L Feringa
Journal: Acc Chem Res Date: 2000-06 Impact factor: 22.384

7. Enantioselective synthesis of near enantiopure compound by asymmetric autocatalysis triggered by asymmetric photolysis with circularly polarized light.

Authors: Tsuneomi Kawasaki; Mirai Sato; Saori Ishiguro; Takahiro Saito; Yosuke Morishita; Itaru Sato; Hideo Nishino; Yoshihisa Inoue; Kenso Soai
Journal: J Am Chem Soc Date: 2005-03-16 Impact factor: 15.419

8. Palladium(0)-catalyzed synthesis of chiral ene-allenes using alkenyl trifluoroborates.

Authors: Gary A Molander; Erin M Sommers; Sharon R Baker
Journal: J Org Chem Date: 2006-02-17 Impact factor: 4.354

9. Direct and stereospecific synthesis of allenes via reduction of propargylic alcohols with Cp2Zr(H)Cl.

Authors: Xiaotao Pu; Joseph M Ready
Journal: J Am Chem Soc Date: 2008-07-25 Impact factor: 15.419

10. Unprecedented selectivity via electronic substrate recognition in the 1,4-addition to cyclic olefins using a chiral disulfoxide rhodium catalyst.

Authors: Justus J Bürgi; Ronaldo Mariz; Michele Gatti; Emma Drinkel; Xinjun Luan; Sascha Blumentritt; Anthony Linden; Reto Dorta
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

13 in total

1. Rhodium(I)/diene-catalyzed addition reactions of arylborons with ketones.

Authors: Yuan-Xi Liao; Chun-Hui Xing; Qiao-Sheng Hu
Journal: Org Lett Date: 2012-03-01 Impact factor: 6.005

2. Synthesis of Complex Glycolates by Enantioconvergent Addition Reactions.

Authors: Samuel L Bartlett; Jeffrey S Johnson
Journal: Acc Chem Res Date: 2017-08-17 Impact factor: 22.384

3. Synthesis of Complex Tertiary Glycolates by Enantioconvergent Arylation of Stereochemically Labile α-Keto Esters.

Authors: Samuel L Bartlett; Kimberly M Keiter; Jeffrey S Johnson
Journal: J Am Chem Soc Date: 2017-03-02 Impact factor: 15.419

4. 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

5. Ru-Catalyzed Asymmetric Addition of Arylboronic Acids to Aliphatic Aldehydes via P-Chiral Monophosphorous Ligands.

Authors: Rui Miao; Yanping Xia; Yifei Wei; Lu Ouyang; Renshi Luo
Journal: Molecules Date: 2022-06-17 Impact factor: 4.927

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

Authors: Ian T Crouch; Robynne K Neff; Doug E Frantz
Journal: J Am Chem Soc Date: 2013-03-19 Impact factor: 15.419

7. Organocatalytic synthesis of chiral tetrasubstituted allenes from racemic propargylic alcohols.

Authors: Deyun Qian; LinLin Wu; Zhenyang Lin; Jianwei Sun
Journal: Nat Commun Date: 2017-09-18 Impact factor: 14.919

8. Access to enantioenriched compounds bearing challenging tetrasubstituted stereocenters via kinetic resolution of auxiliary adjacent alcohols.

Authors: Shengtong Niu; Hao Zhang; Weici Xu; Prasanta Ray Bagdi; Guoxiang Zhang; Jinggong Liu; Shuang Yang; Xinqiang Fang
Journal: Nat Commun Date: 2021-06-18 Impact factor: 14.919

9. A palladium-catalyzed approach to allenic aromatic ethers and first total synthesis of terricollene A.

Authors: Chaofan Huang; Fuchun Shi; Yifan Cui; Can Li; Jie Lin; Qi Liu; Anni Qin; Huanan Wang; Guolin Wu; Penglin Wu; Junzhe Xiao; Haibo Xu; Yuan Yuan; Yizhan Zhai; Wei-Feng Zheng; Yangguangyan Zheng; Biao Yu; Shengming Ma
Journal: Chem Sci Date: 2021-06-09 Impact factor: 9.825

10. Enantiodivergent Synthesis of Allenes by Point-to-Axial Chirality Transfer.

Authors: Roly J Armstrong; Meganathan Nandakumar; Rafael M P Dias; Adam Noble; Eddie L Myers; Varinder K Aggarwal
Journal: Angew Chem Int Ed Engl Date: 2018-05-30 Impact factor: 15.336