Journal of the American Chemical Society
DOI: 10.1021/jacs.2c11466
Iakovos Saridakis
Shared posts
25 Feb 23:58
[ASAP] “Four-In-One” Design of a Hemicyanine-Based Modular Scaffold for High-Contrast Activatable Molecular Afterglow Imaging
by Yongchao Liu, Lili Teng, Xiao-Feng Lou, Xiao-Bing Zhang, and Guosheng Song
04 Jan 10:14
[ASAP] Thermal and (Thermo-Reversible) Photochemical Cycloisomerization of 1H‑2-Benzo[c]oxocins: From Synthetic Applications to the Development of a New T‑Type Molecular Photoswitch
by Minghui Zhou, Simon Mathew, and Bas de Bruin
Journal of the American Chemical Society
DOI: 10.1021/jacs.2c11310
27 Oct 06:56
[ASAP] Enantioselective Synthesis of N‑Benzylic Heterocycles by Ni/Photoredox Dual Catalysis
by Caitlin R. Lacker, Travis J. DeLano, Emily P. Chen, Jongrock Kong, Kevin M. Belyk, Tiffany Piou, and Sarah E. Reisman
Journal of the American Chemical Society
DOI: 10.1021/jacs.2c07917
Josep Mas Roselló, Bruna and 5 others like this
17 Aug 06:41
[ASAP] Synthesis of Tertiary Amines through Extrusive Alkylation of Carbamates
by Guoliang Zhang, David Favela, Winston L. Chow, Rishab N. Iyer, Alexander J. Pell, and David E. Olson
Organic Letters
DOI: 10.1021/acs.orglett.2c02516
Jordan McCone, QiuJ and one other like this
08 Aug 08:49
Practical Synthesis of Chiral Allylboronates by Asymmetric 1,1‐Difunctionalization of Terminal Alkenes
by Caocao Sun,
Yuqiang Li,
Guoyin Yin
A highly 1,1-regio- and enantioselective alkenylboration of undirected and unactivated alkenes has been developed, which allows chiral allylboronates to be efficiently synthesized from readily available terminal alkenes, alkenyl bromides and B2pin2. This method is distinguished by its use of an inexpensive chiral catalyst, readily available starting materials, mild and convenient reaction conditions, scalability and practicality.
Abstract
We report herein a modular catalytic method for the efficient enantioselective synthesis of chiral allylboronates from abundant feedstock chemicals through an asymmetric 1,1-difunctionalization of alkenes. This protocol is distinguished by its use of an inexpensive chiral catalyst, mild and convenient reaction conditions, wide substrate scope, scalability and practicality. The utility of this method is demonstrated by the rapid synthesis of key intermediates of complex drug molecules. Mechanistic studies reveal that β-H elimination is a highly regioselective step and the reversible homolysis and convergance to the lower energy pre-reductive elimination intermediate is the enantio-determining step.
11 Nov 22:22
[ASAP] Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis
by Nicholas E. S. Tay, Dan Lehnherr, and Tomislav Rovis
Chemical Reviews
DOI: 10.1021/acs.chemrev.1c00384
Shoukun Zhang, M. L. Lepage and 9 others like this
04 Nov 13:14
[ASAP] Photocatalytic Hydroaminoalkylation of Styrenes with Unprotected Primary Alkylamines
by Hannah E. Askey, James D. Grayson, Joshua D. Tibbetts, Jacob C. Turner-Dore, Jake M. Holmes, Gabriele Kociok-Kohn, Gail L. Wrigley, and Alexander J. Cresswell
Journal of the American Chemical Society
DOI: 10.1021/jacs.1c07401
Sebastian Beil, erlyj2006 and 3 others like this
30 Oct 10:44
[ASAP] Organogermanes as Orthogonal Coupling Partners in Synthesis and Catalysis
by Christoph Fricke and Franziska Schoenebeck
Accounts of Chemical Research
DOI: 10.1021/acs.accounts.0c00527
123rliu likes this
08 Oct 21:40
[ASAP] Review of Underexplored Medicinal Plants from Sub-Saharan Africa Underexplored Medicinal Plants from Sub-Saharan Africa: Plants with Therapeutic Potential for Human Health, 1st edition. Edited by Namrita Lall. Academic Press: San Diego, CA. 2019. Paperback; xxxiv + 358 pp. $125.00 for either paperback or ebook. ISBN 978-0-12-816814-1.
by Lesley-Ann Giddings
Journal of Natural Products
DOI: 10.1021/acs.jnatprod.0c00992
05 Aug 21:32
[ASAP] Fluorinated Ylides/Carbenes and Related Intermediates from Phosphonium/Sulfonium Salts
by Jin-Hong Lin and Ji-Chang Xiao*
Accounts of Chemical Research
DOI: 10.1021/acs.accounts.0c00244
erlyj2006, Iakovos Saridakis and -1 others like this
13 Dec 11:22
[ASAP] Synthesis of Dibenzo[d,f][1,3]Diazepines via Elemental Sulfur-Mediated Cyclocondensation of 2,2'-Biphenyldiamines with 2-Chloroacetic Acid Derivatives
by Tatyana A. Tikhonova†, Konstantin A. Lyssenko‡§, Igor V. Zavarzin†, and Yulia A. Volkova*†
The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.9b02002
29 Nov 20:42
Peptide‐Chain Elongation Using Unprotected Amino Acids in a Micro‐Flow Reactor
by Shinichiro Fuse,
Koshiro Masuda,
Yuma Otake,
Hiroyuki Nakamura
Who needs protection! Peptide synthesis using unprotected amino acids via mixed carbonic anhydride was demonstrated (see figure). Micro‐flow technology enabled rapid mixing of an organic layer containing a protected amino acid or dipeptide and an aqueous layer containing an unprotected amino acid or dipeptide to accelerate the desired amidation without severe racemization/epimerization (≤0.4 %). Various peptides were obtained in good yields using inexpensive, less toxic, and less wasteful reagents.
Abstract
Conventional peptide synthesis requires a deprotection step after each amidation step, which decreases synthetic efficiency. Therefore, peptide synthesis using unprotected amino acids is considered an ideal approach. Here, we report peptide chain elongation using unprotected amino acids via a mixed carbonic anhydride. Micro‐flow technology enabled rapid mixing of an organic layer containing a protected amino acid or dipeptide and an aqueous layer containing an unprotected amino acid or dipeptide to accelerate the desired amidation, and this approach successfully suppressed undesired racemization/epimerization (≤0.4 %). Various di‐, tri‐, and tetra‐peptides were obtained in good to high yields. This is the first report on peptide chain elongation that proceeds without severe racemization from unprotected amino acids using inexpensive, nonexplosive, less wasteful, and less toxic reagents.
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