Literature DB >> 28467031

Palladium-Catalyzed Enantioselective Redox-Relay Heck Alkynylation of Alkenols To Access Propargylic Stereocenters.

Zhi-Min Chen1, Christine S Nervig1, Ryan J DeLuca1, Matthew S Sigman1.   

Abstract

An enantioselective redox-relay Heck alkynylation of di- and trisubstituted alkenols to construct propargylic stereocenters is disclosed using a new pyridine oxazoline ligand. This strategy allows direct access to chiral β-alkynyl carbonyl compounds employing allylic alcohol substrates in contrast to more traditional conjugate addition methods.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Heck reaction; alkenes; alkynylation; propargylic stereocenter

Mesh：

Substances：

Year:  2017        PMID： 28467031      PMCID： PMC5528850          DOI： 10.1002/anie.201703089

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


  41 in total

1.  Palladium-catalyzed cross-coupling: a historical contextual perspective to the 2010 Nobel Prize.

Authors:  Carin C C Johansson Seechurn; Matthew O Kitching; Thomas J Colacot; Victor Snieckus
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-09       Impact factor: 15.336

2.  Asymmetric synthesis of beta-alkynyl aldehydes by rhodium-catalyzed conjugate alkynylation.

Authors:  Takahiro Nishimura; Takahiro Sawano; Tamio Hayashi
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

3.  The asymmetric Heck and related reactions.

Authors:  Dennis Mc Cartney; Patrick J Guiry
Journal:  Chem Soc Rev       Date:  2011-06-15       Impact factor: 54.564

4.  Enantioselective zinc-mediated conjugate addition of terminal alkynes to enones.

Authors:  Gonzalo Blay; Luz Cardona; José R Pedro; Amparo Sanz-Marco
Journal:  Chemistry       Date:  2012-08-31       Impact factor: 5.236

5.  Palladium-catalyzed enantioselective Heck alkenylation of acyclic alkenols using a redox-relay strategy.

Authors:  Harshkumar H Patel; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2015-03-09       Impact factor: 15.419

6.  Enantioselective Palladium-Catalyzed Alkenylation of Trisubstituted Alkenols To Form Allylic Quaternary Centers.

Authors:  Harshkumar H Patel; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2016-10-25       Impact factor: 15.419

7.  Ni(II)-catalyzed enantioselective conjugate addition of acetylenes to alpha,beta-enones.

Authors:  Oleg V Larionov; E J Corey
Journal:  Org Lett       Date:  2010-01-15       Impact factor: 6.005

8.  Room-temperature decarboxylative alkynylation of carboxylic acids using photoredox catalysis and EBX reagents.

Authors:  Franck Le Vaillant; Thibaut Courant; Jerome Waser
Journal:  Angew Chem Int Ed Engl       Date:  2015-07-24       Impact factor: 15.336

9.  Asymmetric Conjugate Alkynylation of Cyclic α,β-Unsaturated Carbonyl Compounds with a Chiral Diene Rhodium Catalyst.

Authors:  Xiaowei Dou; Yinhua Huang; Tamio Hayashi
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-04       Impact factor: 15.336

10.  A general, practical palladium-catalyzed cyanation of (hetero)aryl chlorides and bromides.

Authors:  Todd D Senecal; Wei Shu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2013-08-09       Impact factor: 15.336
View more
  6 in total

1.  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

2.  Development and Mechanistic Interrogation of Interrupted Chain-Walking in the Enantioselective Relay Heck Reaction.

Authors:  Sean P Ross; Ajara A Rahman; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2020-05-29       Impact factor: 15.419

3.  Palladium-Catalyzed Enantioselective Relay Heck Arylation of Enelactams: Accessing α,β-Unsaturated δ-Lactams.

Authors:  Qianjia Yuan; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2018-05-16       Impact factor: 15.419

Review 4.  Walking Metals for Remote Functionalization.

Authors:  Heiko Sommer; Francisco Juliá-Hernández; Ruben Martin; Ilan Marek
Journal:  ACS Cent Sci       Date:  2018-02-08       Impact factor: 14.553

5.  Mechanistic Insights on the Selectivity of the Tandem Heck-Ring-Opening of Cyclopropyldiol Derivatives.

Authors:  Anthony Cohen; Alexander Kaushansky; Ilan Marek
Journal:  JACS Au       Date:  2022-03-05

Review 6.  Stereoselective Remote Functionalization via Palladium-Catalyzed Redox-Relay Heck Methodologies.

Authors:  Holly E Bonfield; Damien Valette; David M Lindsay; Marc Reid
Journal:  Chemistry       Date:  2020-10-08       Impact factor: 5.236
  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.