Literature DB >> 21892499

Use of alkyl 2,4,6-triisopropylbenzoates in the asymmetric homologation of challenging boronic esters.

Robin Larouche-Gauthier1, Catherine J Fletcher, Irantzu Couto, Varinder K Aggarwal.   

Abstract

(-)-Sparteine induced lithiation of primary 2,4,6-triisopropylbenzoates and subsequent homologation of boronic esters is reported. A comparative study with lithiated N,N-diisopropylcarbamates has demonstrated the superiority of the hindered benzoate.

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Year:  2011        PMID： 21892499     DOI： 10.1039/c1cc14469c

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  15 in total

1.  Single-electron transmetalation: an enabling technology for secondary alkylboron cross-coupling.

Authors:  David N Primer; Idris Karakaya; John C Tellis; Gary A Molander
Journal:  J Am Chem Soc       Date:  2015-02-04       Impact factor: 15.419

2.  Ru-Catalyzed Asymmetric Addition of Arylboronic Acids to Aliphatic Aldehydes via P-Chiral Monophosphorous Ligands.

Authors:  Rui Miao; Yanping Xia; Yifei Wei; Lu Ouyang; Renshi Luo
Journal:  Molecules       Date:  2022-06-17       Impact factor: 4.927

3.  Regio- and Stereoselective Homologation of 1,2-Bis(Boronic Esters): Stereocontrolled Synthesis of 1,3-Diols and Sch 725674.

Authors:  Alexander Fawcett; Dominik Nitsch; Muhammad Ali; Joseph M Bateman; Eddie L Myers; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-26       Impact factor: 15.336

4.  Short Enantioselective Total Synthesis of Tatanan A and 3-epi-Tatanan A Using Assembly-Line Synthesis.

Authors:  Adam Noble; Stefan Roesner; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2016-11-16       Impact factor: 15.336

5.  Alkynyl Moiety for Triggering 1,2-Metallate Shifts: Enantiospecific sp2 -sp3 Coupling of Boronic Esters with p-Arylacetylenes.

Authors:  Venkataraman Ganesh; Marcin Odachowski; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-12       Impact factor: 15.336

6.  Mechanistic Insights into Carbonyl-Directed Rhodium-Catalyzed Hydroboration: ab Initio Study of a Cyclic γ,δ-Unsaturated Amide.

Authors:  Zhao-Di Yang; Rhitankar Pal; Gia L Hoang; Xiao Cheng Zeng; James M Takacs
Journal:  ACS Catal       Date:  2014-01-22       Impact factor: 13.084

7.  Assembly-line synthesis of organic molecules with tailored shapes.

Authors:  Matthew Burns; Stéphanie Essafi; Jessica R Bame; Stephanie P Bull; Matthew P Webster; Sébastien Balieu; James W Dale; Craig P Butts; Jeremy N Harvey; Varinder K Aggarwal
Journal:  Nature       Date:  2014-09-11       Impact factor: 49.962

8.  Enantiospecific Alkynylation of Alkylboronic Esters.

Authors:  Yahui Wang; Adam Noble; Eddie L Myers; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2016-03-02       Impact factor: 15.336

9.  Tandem Allylboration-Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (-)-Clavosolide A.

Authors:  Alba Millán; James R Smith; Jack L-Y Chen; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2016-01-14       Impact factor: 15.336

10.  Enantioselective installation of adjacent tertiary benzylic stereocentres using lithiation-borylation-protodeboronation methodology. Application to the synthesis of bifluranol and fluorohexestrol.

Authors:  Stefan Roesner; Daniel J Blair; Varinder K Aggarwal
Journal:  Chem Sci       Date:  2015-04-28       Impact factor: 9.825
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