Literature DB >> 23886015

Enantioselective synthesis of anti homoallylic alcohols from terminal alkynes and aldehydes based on concomitant use of a cationic iridium complex and a chiral phosphoric acid.

Tomoya Miura1, Yui Nishida, Masao Morimoto, Masahiro Murakami.   

Abstract

We report a highly diastereo- and enantioselective synthesis of anti homoallylic alcohols from terminal alkynes via (E)-1-alkenylboronates based upon two catalytic reactions: a cationic iridium complex-catalyzed olefin transposition of (E)-1-alkenylboronates and a chiral phosphoric acid-catalyzed allylation reaction of aldehydes.

Entities:  

Year:  2013        PMID： 23886015     DOI： 10.1021/ja405790t

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


  16 in total

1.  Selection between Diastereomeric Kinetic vs Thermodynamic Carbonyl Binding Modes Enables Enantioselective Iridium-Catalyzed anti-(α-Aryl)allylation of Aqueous Fluoral Hydrate and Difluoroacetaldehyde Ethyl Hemiacetal.

Authors:  James M Cabrera; Johannes Tauber; Wandi Zhang; Ming Xiang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2018-07-18       Impact factor: 15.419

Review 2.  Remote functionalization through alkene isomerization.

Authors:  Alexandre Vasseur; Jeffrey Bruffaerts; Ilan Marek
Journal:  Nat Chem       Date:  2016-03       Impact factor: 24.427

3.  Enantioselective ruthenium-catalyzed carbonyl allylation via alkyne-alcohol C-C bond-forming transfer hydrogenation: allene hydrometalation vs oxidative coupling.

Authors:  Tao Liang; Khoa D Nguyen; Wandi Zhang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-03-03       Impact factor: 15.419

4.  Diastereo-, Enantio-, and anti-Selective Formation of Secondary Alcohol and Quaternary Carbon Stereocenters by Cu-Catalyzed Additions of B-Substituted Allyl Nucleophiles to Carbonyls.

Authors:  Emilie Wheatley; Joseph M Zanghi; Simon J Meek
Journal:  Org Lett       Date:  2020-11-18       Impact factor: 6.005

5.  Ruthenium Catalyzed Diastereo- and Enantioselective Coupling of Propargyl Ethers with Alcohols: Siloxy-Crotylation via Hydride Shift Enabled Conversion of Alkynes to π-Allyls.

Authors:  Tao Liang; Wandi Zhang; Te-Yu Chen; Khoa D Nguyen; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-09-29       Impact factor: 15.419

6.  Iridium-Catalyzed C-C Coupling of a Simple Propargyl Ether with Primary Alcohols: Enantioselective Homoaldol Addition via Redox-Triggered (Z)-Siloxyallylation.

Authors:  Tao Liang; Wandi Zhang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-12-15       Impact factor: 15.419

7.  Ruthenium-Catalyzed Multicomponent Reactions: Access to α-Silyl-β-Hydroxy Vinylsilanes, Stereodefined 1,3-Dienes, and Cyclohexenes.

Authors:  Barry M Trost; Dennis C Koester; Ehesan U Sharif
Journal:  Chemistry       Date:  2016-01-25       Impact factor: 5.236

8.  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

9.  Diastereo- and Enantioselective Ruthenium-Catalyzed C-C Coupling of 1-Arylpropynes and Alcohols: Alkynes as Chiral Allylmetal Precursors in Carbonyl anti-(α-Aryl)allylation.

Authors:  Ming Xiang; Ankan Ghosh; Michael J Krische
Journal:  J Am Chem Soc       Date:  2021-02-08       Impact factor: 15.419

10.  Ru-catalyzed isomerization of ω-alkenylboronates towards stereoselective synthesis of vinylboronates with subsequent in situ functionalization.

Authors:  Guo-Ming Ho; Lucas Segura; Ilan Marek
Journal:  Chem Sci       Date:  2020-05-26       Impact factor: 9.825
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