Literature DB >> 24915514

Catalytic functionalization of tertiary alcohols to fully substituted carbon centres.

Long Chen1, Xiao-Ping Yin, Cui-Hong Wang, Jian Zhou.   

Abstract

The catalytic nucleophilic substitution of tertiary alcohols using carbon or heteroatom based nucleophiles is a versatile methodology for the efficient, diverse and atom economical construction of fully substituted carbon centres, including both quaternary carbons and heteroatom substituted tetrasubstituted carbons, which only produces water as the by-product. This review summarizes the recent progress in this field, including the catalytic asymmetric studies and their application in the natural product synthesis, briefly discusses the reaction mechanism and challenges, and outlines synthetic opportunities that are still open.

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Year:  2014        PMID: 24915514     DOI: 10.1039/c4ob00718b

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  7 in total

1.  Electroreductive Olefin-Ketone Coupling.

Authors:  Pengfei Hu; Byron K Peters; Christian A Malapit; Julien C Vantourout; Pan Wang; Jinjun Li; Lucas Mele; Pierre-Georges Echeverria; Shelley D Minteer; Phil S Baran
Journal:  J Am Chem Soc       Date:  2020-12-01       Impact factor: 15.419

2.  Structurally Divergent Lithium Catalyzed Friedel-Crafts Reactions on Oxetan-3-ols: Synthesis of 3,3-Diaryloxetanes and 2,3-Dihydrobenzofurans.

Authors:  Rosemary A Croft; James J Mousseau; Chulho Choi; James A Bull
Journal:  Chemistry       Date:  2016-10-10       Impact factor: 5.236

3.  Lewis Acid Catalyzed Transfer Hydromethallylation for the Construction of Quaternary Carbon Centers.

Authors:  Johannes C L Walker; Martin Oestreich
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-12       Impact factor: 15.336

4.  Isothiourea-Catalyzed Acylative Kinetic Resolution of Tertiary α-Hydroxy Esters.

Authors:  Shen Qu; Samuel M Smith; Víctor Laina-Martín; Rifahath M Neyyappadath; Mark D Greenhalgh; Andrew D Smith
Journal:  Angew Chem Int Ed Engl       Date:  2020-07-16       Impact factor: 15.336

5.  Synergistic Brønsted/Lewis acid catalyzed aromatic alkylation with unactivated tertiary alcohols or di-tert-butylperoxide to synthesize quaternary carbon centers.

Authors:  Aaron Pan; Maja Chojnacka; Robert Crowley; Lucas Göttemann; Brandon E Haines; Kevin G M Kou
Journal:  Chem Sci       Date:  2022-03-08       Impact factor: 9.825

6.  Alcohols as Alkylating Agents in the Cation-Induced Formation of Nitrogen Heterocycles.

Authors:  Lydia Cox; Yuxiang Zhu; Philip J Smith; Kirsten E Christensen; Mireia Sidera Portela; Timothy J Donohoe
Journal:  Angew Chem Int Ed Engl       Date:  2022-07-13       Impact factor: 16.823

7.  Chemical Space Exploration of Oxetanes.

Authors:  Fernando Rodrigues de Sá Alves; Rafael M Couñago; Stefan Laufer
Journal:  Int J Mol Sci       Date:  2020-11-02       Impact factor: 5.923

  7 in total

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