Efficient, Flexible Synthesis of Molecules with Tailored Shapes: from Photo-switchable Helices to anti-Cancer Compounds

Informazioni relative al progetto

FRESCO

ID dell’accordo di sovvenzione: 670668

DOI 10.3030/670668

Progetto chiuso

Data della firma CE 15 Giugno 2015

Data di avvio 1 Ottobre 2015

Data di completamento 31 Marzo 2021

Finanziato da

• EXCELLENT SCIENCE - European Research Council (ERC)

Costo totale € 2 436 379,00

Contributo UE € 2 436 379,00

Coordinato da

UNIVERSITY OF BRISTOL
United Kingdom

Pubblicazioni

Peer reviewed articles (39)

Difunctionalization of C–C σ-Bonds Enabled by the Reaction of Bicyclo[1.1.0]butyl Boronate Complexes with Electrophiles: Reaction Development, Scope, and Stereochemical Origins

Autori: Steven H. Bennett, Alexander Fawcett, Elliott H. Denton, Tobias Biberger, Valerio Fasano, Nils Winter, Varinder K. Aggarwal
Pubblicato in: Journal of the American Chemical Society, Numero 142/39, 2020, Pagina/e 16766-16775, ISSN 0002-7863
Editore: American Chemical Society
DOI: 10.1021/jacs.0c07357

Conformationally Controlled Linear and Helical Hydrocarbons Bearing Extended Side Chains.

Autori: Lin Guo; Oliver J. Dutton; Murat Kucukdisli; Matthew Davy; Olivier Wagnières; Craig P. Butts; Eddie L. Myers; Varinder K. Aggarwal
Pubblicato in: Journal of the American Chemical Society, Numero 143/40, 2021, Pagina/e 16682-16692, ISSN 0002-7863
Editore: American Chemical Society
DOI: 10.1021/jacs.1c07778

Divergent, Strain‐Release Reactions of Azabicyclo[1.1.0]butyl Carbinols: Semipinacol or Spiroepoxy Azetidine Formation

Autori: Charlotte H. U. Gregson, Adam Noble, Varinder K. Aggarwal
Pubblicato in: Angewandte Chemie International Edition, Numero 60/13, 2021, Pagina/e 7360-7365, ISSN 1433-7851
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/anie.202100583

Enantiospecific Synthesis of ortho -Substituted Benzylic Boronic Esters by a 1,2-Metalate Rearrangement/1,3-Borotropic Shift Sequence

Autori: Stefan Aichhorn, Raphael Bigler, Eddie L. Myers, Varinder K. Aggarwal
Pubblicato in: Journal of the American Chemical Society, Numero 139/28, 2017, Pagina/e 9519-9522, ISSN 0002-7863
Editore: American Chemical Society
DOI: 10.1021/jacs.7b05880

Enantioselective Rhodium(III)-Catalyzed Markovnikov Hydroboration of Unactivated Terminal Alkenes

Autori: James R. Smith, Beatrice S. L. Collins, Matthew J. Hesse, Mark A. Graham, Eddie L. Myers, Varinder K. Aggarwal
Pubblicato in: Journal of the American Chemical Society, Numero 139/27, 2017, Pagina/e 9148-9151, ISSN 0002-7863
Editore: American Chemical Society
DOI: 10.1021/jacs.7b05149

Photoinduced decarboxylative borylation of carboxylic acids

Autori: Alexander Fawcett, Johan Pradeilles, Yahui Wang, Tatsuya Mutsuga, Eddie L. Myers, Varinder K. Aggarwal
Pubblicato in: Science, Numero 357/6348, 2017, Pagina/e 283-286, ISSN 0036-8075
Editore: American Association for the Advancement of Science
DOI: 10.1126/science.aan3679

50 Years of Zweifel Olefination: A Transition-Metal-Free Coupling

Autori: Varinder Aggarwal, Roly Armstrong
Pubblicato in: Synthesis, Numero 49/15, 2017, Pagina/e 3323-3336, ISSN 0039-7881
Editore: Georg Thieme Verlag
DOI: 10.1055/s-0036-1589046

Synergy of synthesis, computation and NMR reveals correct baulamycin structures

Autori: Jingjing Wu, Paula Lorenzo, Siying Zhong, Muhammad Ali, Craig P. Butts, Eddie L. Myers, Varinder K. Aggarwal
Pubblicato in: Nature, Numero 547/7664, 2017, Pagina/e 436-440, ISSN 0028-0836
Editore: Nature Publishing Group
DOI: 10.1038/nature23265

Asymmetric Synthesis of Secondary and Tertiary Boronic Esters

Autori: Beatrice S. L. Collins, Claire M. Wilson, Eddie L. Myers, Varinder K. Aggarwal
Pubblicato in: Angewandte Chemie International Edition, Numero 56/39, 2017, Pagina/e 11700-11733, ISSN 1433-7851
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201701963

Stereospecific Allylic Functionalization: The Reactions of Allylboronate Complexes with Electrophiles

Autori: Cristina García-Ruiz, Jack L.-Y. Chen, Christopher Sandford, Kathryn Feeney, Paula Lorenzo, Guillaume Berionni, Herbert Mayr, Varinder K. Aggarwal
Pubblicato in: Journal of the American Chemical Society, Numero 139/43, 2017, Pagina/e 15324-15327, ISSN 0002-7863
Editore: American Chemical Society
DOI: 10.1021/jacs.7b10240

Enantiospecific sp 2 -sp 3 Coupling of ortho - and para -Phenols with Secondary and Tertiary Boronic Esters

Autori: Claire M. Wilson, Venkataraman Ganesh, Adam Noble, Varinder K. Aggarwal
Pubblicato in: Angewandte Chemie International Edition, Numero 56/51, 2017, Pagina/e 16318-16322, ISSN 1433-7851
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201710777

Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides

Autori: Oleksandr Zhurakovskyi, Yunus E. Türkmen, Lorenz E. Löffler, Vijayalakshmi A. Moorthie, C. Chun Chen, Michael A. Shaw, Mark R. Crimmin, Marco Ferrara, Mushtaq Ahmad, Mehrnoosh Ostovar, Johnathan V. Matlock, Varinder K. Aggarwal
Pubblicato in: Angewandte Chemie International Edition, Numero 57/5, 2018, Pagina/e 1346-1350, ISSN 1433-7851
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201712065

Enantiospecific Three-Component Alkylation of Furan and Indole

Autori: Mattia Silvi, Raffael Schrof, Adam Noble, Varinder K. Aggarwal
Pubblicato in: Chemistry - A European Journal, Numero 24/17, 2018, Pagina/e 4279-4282, ISSN 0947-6539
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/chem.201800527

Stereocontrolled Synthesis of Polypropionate Fragments based on a Building Block Assembly Strategy using Lithiation-Borylation Methodologies

Autori: Alba Millán, Pablo D. Grigol Martinez, Varinder K. Aggarwal
Pubblicato in: Chemistry - A European Journal, Numero 24/3, 2018, Pagina/e 730-735, ISSN 0947-6539
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/chem.201704946

α-Sulfinyl Benzoates as Precursors to Li and Mg Carbenoids for the Stereoselective Iterative Homologation of Boronic Esters

Autori: Giorgia Casoni, Murat Kucukdisli, James M. Fordham, Matthew Burns, Eddie L. Myers, Varinder K. Aggarwal
Pubblicato in: Journal of the American Chemical Society, Numero 139/34, 2017, Pagina/e 11877-11886, ISSN 0002-7863
Editore: American Chemical Society
DOI: 10.1021/jacs.7b05457

Visible-Light-Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ-Amino Boronic Esters

Autori: Adam Noble, Riccardo S. Mega, Daniel Pflästerer, Eddie L. Myers, Varinder K. Aggarwal
Pubblicato in: Angewandte Chemie International Edition, Numero 57/8, 2018, Pagina/e 2155-2159, ISSN 1433-7851
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201712186

Photoinduced Deaminative Borylation of Alkylamines

Autori: Jingjing Wu, Lin He, Adam Noble, Varinder K. Aggarwal
Pubblicato in: Journal of the American Chemical Society, Numero 140, 2018, Pagina/e 10700–10704, ISSN 0002-7863
Editore: American Chemical Society
DOI: 10.1021/jacs.8b07103

Stereo- and Regiocontrolled Methylboration of Terminal Alkynes

Autori: Oleksandr Zhurakovskyi, Rafael M. P. Dias, Adam Noble, Varinder K. Aggarwal
Pubblicato in: Organic Letters, Numero 20/10, 2018, Pagina/e 3136-3139, ISSN 1523-7060
Editore: American Chemical Society
DOI: 10.1021/acs.orglett.8b01252

Complex Boron-Containing Molecules through a 1,2-Metalate Rearrangement/anti-S N 2′ Elimination/Cycloaddition Reaction Sequence

Autori: Varinder Aggarwal, Chloe Tillin, Raphael Bigler, Renata Calo-Lapido, Beatrice Collins, Adam Noble
Pubblicato in: Synlett, 2018, ISSN 0936-5214
Editore: Georg Thieme Verlag
DOI: 10.1055/s-0037-1610389

Enantiospecific Synthesis of ortho-Substituted 1,1-Diarylalkanes by a 1,2-Metalate Rearrangement/anti-SN2' Elimination/Rearomatizing Allylic Suzuki-Miyaura Reaction Sequence

Autori: Belén Rubial, Beatrice S. L. Collins, Raphael Bigler, Stefan Aichhorn, Adam Noble, Varinder Kumar Aggarwal
Pubblicato in: Angewandte Chemie International Edition, 2018, ISSN 1433-7851
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201811343

Enantiodivergent Synthesis of Allenes by Point-to-Axial Chirality Transfer

Autori: Roly J. Armstrong, Meganathan Nandakumar, Rafael M. P. Dias, Adam Noble, Eddie L. Myers, Varinder K. Aggarwal
Pubblicato in: Angewandte Chemie International Edition, Numero 57/27, 2018, Pagina/e 8203-8208, ISSN 1433-7851
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201804446

Investigation of the Deprotonative Generation and Borylation of Diamine-Ligated α-Lithiated Carbamates and Benzoates by in Situ IR spectroscopy

Autori: Rory C. Mykura, Simon Veth, Ana Varela, Lydia Dewis, Joshua J. Farndon, Eddie L. Myers, Varinder K. Aggarwal
Pubblicato in: Journal of the American Chemical Society, Numero 140/44, 2018, Pagina/e 14677-14686, ISSN 0002-7863
Editore: American Chemical Society
DOI: 10.1021/jacs.8b06871

Chiral Aniline Synthesis via Stereospecific C(sp 3 )–C(sp 2 ) Coupling of Boronic Esters with Aryl Hydrazines

Autori: Venkataraman Ganesh, Adam Noble, Varinder K. Aggarwal
Pubblicato in: Organic Letters, Numero 20/19, 2018, Pagina/e 6144-6147, ISSN 1523-7060
Editore: American Chemical Society
DOI: 10.1021/acs.orglett.8b02615

Synthesis of Functionalized Cyclopropanes from Carboxylic Acids by a Radical Addition-Polar Cyclization Cascade

Autori: Chao Shu, Riccardo S. Mega, Björn J. Andreassen, Adam Noble, Varinder K. Aggarwal
Pubblicato in: Angewandte Chemie International Edition, Numero 57/47, 2018, Pagina/e 15430-15434, ISSN 1433-7851
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201808598

Stereospecific functionalizations and transformations of secondary and tertiary boronic esters

Autori: Christopher Sandford, Varinder K. Aggarwal
Pubblicato in: Chem. Commun., Numero 53/40, 2017, Pagina/e 5481-5494, ISSN 1359-7345
Editore: Royal Society of Chemistry
DOI: 10.1039/C7CC01254C

Full chirality transfer in the synthesis of hindered tertiary boronic esters under in situ lithiation–borylation conditions

Autori: D. J. Blair, S. Zhong, M. J. Hesse, N. Zabaleta, E. L. Myers, V. K. Aggarwal
Pubblicato in: Chem. Commun., Numero 52/30, 2016, Pagina/e 5289-5292, ISSN 1359-7345
Editore: Royal Society of Chemistry
DOI: 10.1039/C6CC00536E

Selective uni- and bidirectional homologation of diborylmethane

Autori: Daniel J. Blair, Damiano Tanini, Joseph M. Bateman, Helen K. Scott, Eddie L. Myers, Varinder K. Aggarwal
Pubblicato in: Chem. Sci., Numero 8/4, 2017, Pagina/e 2898-2903, ISSN 2041-6520
Editore: Royal Society of Chemistry
DOI: 10.1039/C6SC05338F

Iterative assembly line synthesis of polypropionates with full stereocontrol

Autori: Teerawut Bootwicha, Julian M. Feilner, Eddie L. Myers, Varinder K. Aggarwal
Pubblicato in: Nature Chemistry, 2017, ISSN 1755-4330
Editore: Nature Publishing Group
DOI: 10.1038/nchem.2757

Strain-Release-Driven Homologation of Boronic Esters: Application to the Modular Synthesis of Azetidines

Autori: Alexander Fawcett, Amna Murtaza, Charlotte H. U. Gregson, Varinder K. Aggarwal
Pubblicato in: Journal of the American Chemical Society, Numero 141/11, 2019, Pagina/e 4573-4578, ISSN 0002-7863
Editore: American Chemical Society
DOI: 10.1021/jacs.9b01513

Catalyst‐Free Deaminative Functionalizations of Primary Amines by Photoinduced Single‐Electron Transfer

Autori: Jingjing Wu, Phillip S. Grant, Xiabing Li, Adam Noble, Varinder K. Aggarwal
Pubblicato in: Angewandte Chemie International Edition, Numero 58/17, 2019, Pagina/e 5697-5701, ISSN 1433-7851
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201814452

Strain Release of Donor–Acceptor Cyclopropyl Boronate Complexes

Autori: Charlotte H. U. Gregson, Venkataraman Ganesh, Varinder K. Aggarwal
Pubblicato in: Organic Letters, Numero 21/9, 2019, Pagina/e 3412-3416, ISSN 1523-7060
Editore: American Chemical Society
DOI: 10.1021/acs.orglett.9b01152

1,2-Boron Shifts of β-Boryl Radicals Generated from Bis-boronic Esters Using Photoredox Catalysis

Autori: Daniel Kaiser, Adam Noble, Valerio Fasano, Varinder K. Aggarwal
Pubblicato in: Journal of the American Chemical Society, Numero 141/36, 2019, Pagina/e 14104-14109, ISSN 0002-7863
Editore: American Chemical Society
DOI: 10.1021/jacs.9b07564

Photoredox‐Catalyzed Cyclobutane Synthesis by a Deboronative Radical Addition–Polar Cyclization Cascade

Autori: Chao Shu, Adam Noble, Varinder K. Aggarwal
Pubblicato in: Angewandte Chemie International Edition, Numero 58/12, 2019, Pagina/e 3870-3874, ISSN 1433-7851
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201813917

Carbopalladation of C–C σ-bonds enabled by strained boronate complexes

Autori: Alexander Fawcett, Tobias Biberger, Varinder K. Aggarwal
Pubblicato in: Nature Chemistry, Numero 11/2, 2019, Pagina/e 117-122, ISSN 1755-4330
Editore: Nature Publishing Group
DOI: 10.1038/s41557-018-0181-x

Decarboxylative Conjunctive Cross‐coupling of Vinyl Boronic Esters using Metallaphotoredox Catalysis

Autori: Riccardo S. Mega, Vincent K. Duong, Adam Noble, Varinder K. Aggarwal
Pubblicato in: Angewandte Chemie International Edition, Numero 59/11, 2020, Pagina/e 4375-4379, ISSN 1433-7851
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201916340

Photoinduced Deoxygenative Borylations of Aliphatic Alcohols

Autori: Jingjing Wu, Robin M. Bär, Lin Guo, Adam Noble, Varinder K. Aggarwal
Pubblicato in: Angewandte Chemie International Edition, Numero 58/52, 2019, Pagina/e 18830-18834, ISSN 1433-7851
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201910051

Odd–even alternations in helical propensity of a homologous series of hydrocarbons

Autori: Johan A. Pradeilles, Siying Zhong, Márton Baglyas, György Tarczay, Craig P. Butts, Eddie L. Myers, Varinder K. Aggarwal
Pubblicato in: Nature Chemistry, 2020, ISSN 1755-4330
Editore: Nature Publishing Group
DOI: 10.1038/s41557-020-0429-0

Visible-Light-Driven Strain-Increase Ring Contraction Allows the Synthesis of Cyclobutyl Boronic Esters.

Autori: Davenport, Raffael; Silvi, Mattia; Noble, Adam; Hosni, Zied; Fey, Natalie; Aggarwal, Varinder K.
Pubblicato in: Angewandte Chemie International Edition, Numero 59/16, 2020, Pagina/e 6525-6528, ISSN 1433-7851
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201915409

Stereospecific 1,2‐Migrations of Boronate Complexes Induced by Electrophiles

Autori: Hui Wang, Changcheng Jing, Adam Noble, Varinder Kumar Aggarwal
Pubblicato in: Angewandte Chemie International Edition, Numero 59/39, 2020, Pagina/e 16859-16872, ISSN 1433-7851
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/anie.202008096