Literature DB >> 20481453

Copper catalyzed asymmetric propargylation of aldehydes.

Daniel R Fandrick1, Keith R Fandrick, Jonathan T Reeves, Zhulin Tan, Wenjun Tang, Andrew G Capacci, Sonia Rodriguez, Jinhua J Song, Heewon Lee, Nathan K Yee, Chris H Senanayake.   

Abstract

The highly enantio- and regioselective copper catalyzed asymmetric propargylation of aldehydes with a propargyl borolane reagent is reported. The methodology demonstrated broad functional group tolerance and provided high enantioselectivities for aliphatic, vinyl, and aryl aldehydes. The utility of the TMS homopropargylic alcohols was demonstrated by the facile conversion to a chiral dihydropyranone.

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Year:  2010        PMID: 20481453     DOI: 10.1021/ja103312x

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


  16 in total

1.  Catalytic, Enantioselective Synthesis of Allenyl Boronates.

Authors:  De-Wei Gao; Yiyang Xiao; Mingyu Liu; Zhen Liu; Malkanthi K Karunananda; Jason S Chen; Keary M Engle
Journal:  ACS Catal       Date:  2018-03-21       Impact factor: 13.084

2.  Asymmetric propargylation of ketones using allenylboronates catalyzed by chiral biphenols.

Authors:  David S Barnett; Scott E Schaus
Journal:  Org Lett       Date:  2011-07-06       Impact factor: 6.005

3.  Enantioselective synthesis of anti- and syn-homopropargyl alcohols via chiral Brønsted acid catalyzed asymmetric allenylboration reactions.

Authors:  Ming Chen; William R Roush
Journal:  J Am Chem Soc       Date:  2012-06-25       Impact factor: 15.419

4.  Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-Iodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives.

Authors:  Alexander M Sherwood; Samuel E Williamson; Stephanie N Johnson; Anil Yilmaz; Victor W Day; Thomas E Prisinzano
Journal:  J Org Chem       Date:  2018-01-08       Impact factor: 4.354

5.  C-Propargylation Overrides O-Propargylation in Reactions of Propargyl Chloride with Primary Alcohols: Rhodium-Catalyzed Transfer Hydrogenation.

Authors:  Tao Liang; Sang Kook Woo; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-20       Impact factor: 15.336

6.  Sequential C-H Arylation and Enantioselective Hydrogenation Enables Ideal Asymmetric Entry to the Indenopiperidine Core of an 11β-HSD-1 Inhibitor.

Authors:  Xudong Wei; Bo Qu; Xingzhong Zeng; Jolaine Savoie; Keith R Fandrick; Jean-Nicolas Desrosiers; Sergei Tcyrulnikov; Maurice A Marsini; Frederic G Buono; Zhibin Li; Bing-Shiou Yang; Wenjun Tang; Nizar Haddad; Osvaldo Gutierrez; Jun Wang; Heewon Lee; Shengli Ma; Scot Campbell; Jon C Lorenz; Matthias Eckhardt; Frank Himmelsbach; Stefan Peters; Nitinchandra D Patel; Zhulin Tan; Nathan K Yee; Jinhua J Song; Frank Roschangar; Marisa C Kozlowski; Chris H Senanayake
Journal:  J Am Chem Soc       Date:  2016-11-17       Impact factor: 15.419

7.  Brønsted acid catalyzed asymmetric propargylation of aldehydes.

Authors:  Pankaj Jain; Hao Wang; Kendall N Houk; Jon C Antilla
Journal:  Angew Chem Int Ed Engl       Date:  2011-12-28       Impact factor: 15.336

8.  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

9.  Chiral Brønsted acid catalyzed enantioselective synthesis of anti-homopropargyl alcohols via kinetic resolution-aldehyde allenylboration using racemic allenylboronates.

Authors:  Andy S Tsai; Ming Chen; William R Roush
Journal:  Org Lett       Date:  2013-03-13       Impact factor: 6.005

10.  Catalytic Enantioselective Carbonyl Propargylation Beyond Preformed Carbanions: Reductive Coupling and Hydrogen Auto-Transfer.

Authors:  Brett R Ambler; Sang Kook Woo; Michael J Krische
Journal:  ChemCatChem       Date:  2018-08-07       Impact factor: 5.686

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