Literature DB >> 26316158

Synthesis of Adjacent Quaternary Stereocenters by Catalytic Asymmetric Allylboration.

Rauful Alam1, Tobias Vollgraff1, Lars Eriksson1, Kálmán J Szabó1.   

Abstract

Allylboration of ketones with γ-disubstituted allylboronic acids is performed in the presence of chiral BINOL derivatives. The reaction is suitable for single-step creation of adjacent quaternary stereocenters with high selectivity. We show that, with an appropriate choice of the chiral catalyst and the stereoisomeric prenyl substrate, full control of the stereo- and enantioselectivity is possible in the reaction.

Entities:  

Year:  2015        PMID： 26316158     DOI： 10.1021/jacs.5b07498

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


  21 in total

1.  Enantioselective Construction of Acyclic Quaternary Carbon Stereocenters: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Amide Enolates.

Authors:  Pavel Starkov; Jared T Moore; Douglas C Duquette; Brian M Stoltz; Ilan Marek
Journal:  J Am Chem Soc       Date:  2017-07-07       Impact factor: 15.419

2.  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

3.  Enantio- and Diastereoselective Synthesis of Functionalized Carbocycles by Cu-Catalyzed Borylative Cyclization of Alkynes with Ketones.

Authors:  Joseph M Zanghi; Shuang Liu; Simon J Meek
Journal:  Org Lett       Date:  2019-06-14       Impact factor: 6.005

4.  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

5.  Total Synthesis of (+)-Pleuromutilin.

Authors:  Elliot P Farney; Sean S Feng; Felix Schäfers; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2018-01-17       Impact factor: 15.419

6.  Asymmetric Petasis Borono-Mannich Allylation Reactions Catalyzed by Chiral Biphenols.

Authors:  Yao Jiang; Scott E Schaus
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-04       Impact factor: 15.336

7.  Synthesis of Homoallylic Alcohols with Acyclic Quaternary Centers through CoIII -Catalyzed Three-Component C-H Bond Addition to Internally Substituted Dienes and Carbonyls.

Authors:  Sun Dongbang; Zican Shen; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-01       Impact factor: 15.336

8.  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

9.  A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with Terminal Allenes.

Authors:  Erica Y Tsai; Richard Y Liu; Yang Yang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2018-02-02       Impact factor: 15.419

10.  Ruthenium-BINAP Catalyzed Alcohol C-H tert-Prenylation via 1,3-Enyne Transfer Hydrogenation: Beyond Stoichiometric Carbanions in Enantioselective Carbonyl Propargylation.

Authors:  Khoa D Nguyen; Daniel Herkommer; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-04-15       Impact factor: 15.419
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