Literature DB >> 28708391

Enantioselective Synthesis of anti-1,2-Oxaborinan-3-enes from Aldehydes and 1,1-Di(boryl)alk-3-enes Using Ruthenium and Chiral Phosphoric Acid Catalysts.

Tomoya Miura1, Junki Nakahashi1, Wang Zhou1, Yota Shiratori1, Scott G Stewart1, Masahiro Murakami1.   

Abstract

A cationic ruthenium(II) complex catalyzes double-bond transposition of 1,1-di(boryl)alk-3-enes to generate in situ 1,1-di(boryl)alk-2-enes, which then undergo chiral phosphoric acid catalyzed allylation of aldehydes producing homoallylic alcohols with a (Z)-vinylboronate moiety. 1,2-Anti stereochemistry is installed in an enantioselective manner. The (Z)-geometry forged in the products allows their isolation in a form of 1,2-oxaborinan-3-enes, upon which further synthetic transformations are operated.

Entities:  

Year:  2017        PMID： 28708391     DOI： 10.1021/jacs.7b06408

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


  11 in total

1.  Cu-Catalyzed Diastereo- and Enantioselective Reactions of γ,γ-Disubstituted Allyldiboron Compounds with Ketones.

Authors:  Joseph M Zanghi; Simon J Meek
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-24       Impact factor: 15.336

2.  Diastereo- and Enantioselective Synthesis of Homoallylic Amines Bearing Quaternary Carbon Centers.

Authors:  Jacob C Green; Joseph M Zanghi; Simon J Meek
Journal:  J Am Chem Soc       Date:  2020-01-17       Impact factor: 15.419

3.  Synthesis of Quaternary Carbon Stereogenic Centers by Diastereoselective Conjugate Addition of Boron-Stabilized Allylic Nucleophiles to Enones.

Authors:  Michael Z Liang; Simon J Meek
Journal:  J Am Chem Soc       Date:  2020-05-18       Impact factor: 15.419

4.  Catalytic Enantioselective Synthesis of 1,4-Keto-Alkenylboronate Esters and 1,4-Dicarbonyls.

Authors:  Michael Z Liang; Simon J Meek
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-23       Impact factor: 15.336

5.  α-Boryl Organometallic Reagents in Catalytic Asymmetric Synthesis.

Authors:  Chenlong Zhang; Weipeng Hu; James P Morken
Journal:  ACS Catal       Date:  2021-08-12       Impact factor: 13.700

6.  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

7.  1,n-Bisborylalkanes via Radical Boron Migration.

Authors:  Dinghai Wang; Christian Mück-Lichtenfeld; Armido Studer
Journal:  J Am Chem Soc       Date:  2020-05-06       Impact factor: 15.419

8.  A modular and concise approach to MIDA acylboronates via chemoselective oxidation of unsymmetrical geminal diborylalkanes: unlocking access to a novel class of acylborons.

Authors:  Shengjia Lin; Lucia Wang; Negin Aminoleslami; Yanting Lao; Chelsea Yagel; Abhishek Sharma
Journal:  Chem Sci       Date:  2019-03-21       Impact factor: 9.825

9.  α-Silicon effect assisted Curtin-Hammett allylation using allylcopper reagents derived from 1,3-dienylsilanes.

Authors:  Shang Gao; Ming Chen
Journal:  Chem Sci       Date:  2019-06-28       Impact factor: 9.825

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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