Literature DB >> 24735355

Construction of homoallylic alcohols from terminal alkynes and aldehydes with installation of syn-stereochemistry.

Tomoya Miura1, Yui Nishida, Masahiro Murakami.   

Abstract

A cationic rhodium(I) catalyst turns 2-silyl-1-alkenylboronate, readily prepared from a terminal alkyne, into the corresponding allylboronate species, which immediately undergoes nucleophilic addition to an aldehyde to give a syn-homoallylic alcohol stereoselectively.

Entities:  

Year:  2014        PMID： 24735355     DOI： 10.1021/ja502169d

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


  6 in total

1.  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

2.  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

3.  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

4.  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

5.  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

6.  Alkynes as allylmetal equivalents in redox-triggered C-C couplings to primary alcohols: (Z)-homoallylic alcohols via ruthenium-catalyzed propargyl C-H oxidative addition.

Authors:  Boyoung Y Park; Khoa D Nguyen; Mani Raj Chaulagain; Venukrishnan Komanduri; Michael J Krische
Journal:  J Am Chem Soc       Date:  2014-07-30       Impact factor: 15.419
  6 in total

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