Literature DB >> 22298300

Iterative asymmetric allylic substitutions: syn- and anti-1,2-diols through catalyst control.

Jin Kyoon Park1, D Tyler McQuade.   

Abstract

A copper-catalyzed asymmetric allylic boronation (AAB) gives access to syn- and anti-1,2-diols. The method facilitates an iterative strategy for the preparation of polyols, such as the fully differentiated L-ribo-tetrol and protected D-arabino-tetrol. P=protecting group.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID: 22298300     DOI: 10.1002/anie.201107874

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


  11 in total

1.  Catalytic Enantioselective Arylboration of Alkenylarenes.

Authors:  Kaitlyn M Logan; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-21       Impact factor: 15.336

2.  Enantioselective synthesis of boron-substituted quaternary carbon stereogenic centers through NHC-catalyzed conjugate additions of (pinacolato)boron units to enones.

Authors:  Suttipol Radomkit; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2014-02-24       Impact factor: 15.336

3.  Catalyst-Controlled 1,2- and 1,1-Arylboration of α-Alkyl Alkenyl Arenes.

Authors:  Allison M Bergmann; Stanna K Dorn; Kevin B Smith; Kaitlyn M Logan; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-09       Impact factor: 15.336

4.  Practical, Broadly Applicable, α-Selective, Z-Selective, Diastereoselective, and Enantioselective Addition of Allylboron Compounds to Mono-, Di-, Tri-, and Polyfluoroalkyl Ketones.

Authors:  Farid W van der Mei; Changming Qin; Ryan J Morrison; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2017-06-24       Impact factor: 15.419

5.  Catalytic, enantioselective synthesis of 1,2-anti-diols by asymmetric ring-opening/cross-metathesis.

Authors:  John Hartung; Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2014-02-19       Impact factor: 15.336

6.  Mechanism of NHC-Catalyzed Conjugate Additions of Diboron and Borosilane Reagents to α,β-Unsaturated Carbonyl Compounds.

Authors:  Hao Wu; Jeannette M Garcia; Fredrik Haeffner; Suttipol Radomkit; Adil R Zhugralin; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2015-08-11       Impact factor: 15.419

7.  Modular Synthesis of a Versatile Double-Allylation Reagent for Complex Diol Synthesis.

Authors:  Stanna K Dorn; Annika E Tharp; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2021-06-11       Impact factor: 16.823

8.  Cu-catalyzed enantioselective synthesis of tertiary benzylic copper complexes and their in situ addition to carbonyl compounds.

Authors:  Fengchang Cheng; Wenxin Lu; Wei Huang; Lu Wen; Mingfeng Li; Fanke Meng
Journal:  Chem Sci       Date:  2018-04-30       Impact factor: 9.825

9.  Ring-Expanded N-Heterocyclic Carbenes for Copper-Mediated Azide-Alkyne Click Cycloaddition Reactions.

Authors:  Filip Sebest; Jay J Dunsford; Matthew Adams; Jeremy Pivot; Paul D Newman; Silvia Díez-González
Journal:  ChemCatChem       Date:  2018-03-07       Impact factor: 5.686

10.  Concise Synthesis of (S)-δ-CEHC, a Metabolite of Vitamin E.

Authors:  Matthew Burke; Pratik Pal; Peiyi Zhang; Xuan Zhang; Guangrong Zheng
Journal:  ACS Omega       Date:  2021-02-02
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