Literature DB >> 33689214

Ethanol: Unlocking an Abundant Renewable C2 -Feedstock for Catalytic Enantioselective C-C Coupling.

Cole C Meyer1, Nicholas P Stafford1, Melinda J Cheng1, Michael J Krische1.   

Abstract

With annual production at >85 million tons/year, ethanol is the world's largest-volume renewable small molecule carbon source, yet its use as a C2 -feedstock in enantioselective C-C coupling is unknown. Here, the first catalytic enantioselective C-C couplings of ethanol are demonstrated in reactions with structurally complex, nitrogen-rich allylic acetates incorporating the top 10 N-heterocycles found in FDA-approved drugs.
© 2021 Wiley-VCH GmbH.

Entities:  

Keywords:  enantioselectivity; ethanol; hydrogen transfer; iridium; renewable sources

Mesh：

Substances：

Year:  2021        PMID： 33689214      PMCID： PMC8085048          DOI： 10.1002/anie.202102694

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  35 in total

1.  Direct Conversion of Primary Alcohols to 1,2-Amino Alcohols: Enantioselective Iridium-Catalyzed Carbonyl Reductive Coupling of Phthalimido-Allene via Hydrogen Auto-Transfer.

Authors:  Kim Spielmann; Ming Xiang; Leyah A Schwartz; Michael J Krische
Journal:  J Am Chem Soc       Date:  2019-08-29       Impact factor: 15.419

Review 2.  Fluorine in psychedelic phenethylamines.

Authors:  Daniel Trachsel
Journal:  Drug Test Anal       Date:  2012-02-28       Impact factor: 3.345

Review 3.  Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among U.S. FDA approved pharmaceuticals.

Authors:  Edon Vitaku; David T Smith; Jon T Njardarson
Journal:  J Med Chem       Date:  2014-10-07       Impact factor: 7.446

4.  Greener and Sustainable Trends in Synthesis of Organics and Nanomaterials.

Authors:  Rajender S Varma
Journal:  ACS Sustain Chem Eng       Date:  2016-11-07       Impact factor: 8.198

Review 5.  Serotonin and hallucinogens.

Authors:  G K Aghajanian; G J Marek
Journal:  Neuropsychopharmacology       Date:  1999-08       Impact factor: 7.853

6.  Framework towards more Sustainable Chemical Synthesis Design - A Case Study of Organophosphates.

Authors:  Michael A Gonzalez; Sudhakar Takkellapati; Kidus Tadele; Tao Li; Rajender S Varma
Journal:  ACS Sustain Chem Eng       Date:  2019-02-25       Impact factor: 8.198

7.  Iridium-catalyzed coupling reaction of primary alcohols with 1-aryl-1-propynes leading to secondary homoallylic alcohols.

Authors:  Yasushi Obora; Shintaro Hatanaka; Yasutaka Ishii
Journal:  Org Lett       Date:  2009-08-06       Impact factor: 6.005

8.  Elongation of 1,3-polyols via iterative catalyst-directed carbonyl allylation from the alcohol oxidation level.

Authors:  Abbas Hassan; Yu Lu; Michael J Krische
Journal:  Org Lett       Date:  2009-07-16       Impact factor: 6.005

9.  Highly Selective Formation of n-Butanol from Ethanol through the Guerbet Process: A Tandem Catalytic Approach.

Authors:  Sumit Chakraborty; Paige E Piszel; Cassandra E Hayes; R Tom Baker; William D Jones
Journal:  J Am Chem Soc       Date:  2015-11-10       Impact factor: 15.419

10.  Control of Absolute Stereochemistry in Transition-Metal-Catalyzed Hydrogen Borrowing Reactions.

Authors:  Timothy Kwok; Oskar Hoff; Roly J Armstrong; Timothy James Donohoe
Journal:  Chemistry       Date:  2020-04-16       Impact factor: 5.236
View more
  3 in total

1.  Understanding Halide Counterion Effects in Enantioselective Ruthenium-Catalyzed Carbonyl (α-Aryl)allylation: Alkynes as Latent Allenes and Trifluoroethanol-Enhanced Turnover in The Conversion of Ethanol to Higher Alcohols via Hydrogen Auto-transfer.

Authors:  Eliezer Ortiz; Jonathan Z Shezaf; Yu-Hsiang Chang; Théo P Gonçalves; Kuo-Wei Huang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2021-10-04       Impact factor: 16.383

2.  From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future.

Authors:  Catherine Gazolla Santana; Michael J Krische
Journal:  ACS Catal       Date:  2021-04-22       Impact factor: 13.084

3.  Late-Stage C-H Acylation of Tyrosine-Containing Oligopeptides with Alcohols.

Authors:  Iñaki Urruzuno; Paula Andrade-Sampedro; Arkaitz Correa
Journal:  Org Lett       Date:  2021-09-03       Impact factor: 6.005
  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.