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Advances in Stereoselective Synthesis
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Advances in Stereoselective Synthesis

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (28 February 2021) | Viewed by 9153

Special Issue Editor

Prof. Dr. Marcelo Daniel Preite

E-Mail Website
Guest Editor
Facultad de Quimica, Pontificia Universidad Catolica de Chile, VicuñaMackenna 4860, Casilla 306, 7820436 Macul, Santiago, Chile
Interests: organic synthesis; stereoselective synthesis; asymmetric synthesis; chiral auxiliaries and catalysts; main-group metals in synthesis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Stereoselective synthesis in its broadest sense involves the selective introduction of new dissymmetric elements into molecules. As nature is intrinsically dissymmetric, so too are most of the most interesting bioactive molecules, and, therefore, the control of stereoselectivity in organic reactions is always a focus of major interest for most synthetic chemists.

The development of stereoselective methodologies, reagents, and reactions constitute the main topics interest for this Special Issue on “Stereoselective Synthesis”. It is a great pleasure to invite you to submit a contribution on any of these aspects.

Prof. Dr. Marcelo Preite
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Stereoselectivity
  • Regioselectivity
  • Diastereoselectivity
  • Enantioselectivity

Published Papers (3 papers)

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Research

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17 pages, 2074 KiB  
Article
Rate Dependence on Inductive and Resonance Effects for the Organocatalyzed Enantioselective Conjugate Addition of Alkenyl and Alkynyl Boronic Acids to β-Indolyl Enones and β-Pyrrolyl Enones
by Amy Boylan, Thien S. Nguyen, Brian J. Lundy, Jian-Yuan Li, Ravikrishna Vallakati, Sasha Sundstrom and Jeremy A. May
Molecules 2021, 26(6), 1615; https://doi.org/10.3390/molecules26061615 - 14 Mar 2021
Cited by 1 | Viewed by 3167
Abstract
Two key factors bear on reaction rates for the conjugate addition of alkenyl boronic acids to heteroaryl-appended enones: the proximity of inductively electron-withdrawing heteroatoms to the site of bond formation and the resonance contribution of available heteroatom lone pairs to stabilize the developing [...] Read more.
Two key factors bear on reaction rates for the conjugate addition of alkenyl boronic acids to heteroaryl-appended enones: the proximity of inductively electron-withdrawing heteroatoms to the site of bond formation and the resonance contribution of available heteroatom lone pairs to stabilize the developing positive charge at the enone β-position. For the former, the closer the heteroatom is to the enone β-carbon, the faster the reaction. For the latter, greater resonance stabilization of the benzylic cationic charge accelerates the reaction. Thus, reaction rates are increased by the closer proximity of inductive electron-withdrawing elements, but if resonance effects are involved, then increased rates are observed with electron-donating ability. Evidence for these trends in isomeric substrates is presented, and the application of these insights has allowed for reaction conditions that provide improved reactivity with previously problematic substrates. Full article
(This article belongs to the Special Issue Advances in Stereoselective Synthesis)
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10 pages, 1415 KiB  
Article
An Enantioselective Approach to 4-Substituted Proline Scaffolds: Synthesis of (S)-5-(tert-Butoxy carbonyl)-5-azaspiro[2.4]heptane-6-carboxylic Acid
by Blanca López, Martí Bartra, Ramon Berenguer, Xavier Ariza, Jordi Garcia, Roberto Gómez and Hèctor Torralvo
Molecules 2020, 25(23), 5644; https://doi.org/10.3390/molecules25235644 - 30 Nov 2020
Viewed by 2115
Abstract
A catalytic and enantioselective preparation of the (S)-4-methyleneproline scaffold is described. The key reaction is a one-pot double allylic alkylation of an imine analogue of glycine in the presence of a chinchonidine-derived catalyst under phase transfer conditions. These 4-methylene substituted proline [...] Read more.
A catalytic and enantioselective preparation of the (S)-4-methyleneproline scaffold is described. The key reaction is a one-pot double allylic alkylation of an imine analogue of glycine in the presence of a chinchonidine-derived catalyst under phase transfer conditions. These 4-methylene substituted proline derivatives are versatile starting materials often used in medicinal chemistry. In particular, we have transformed tert-butyl (S)-4-methyleneprolinate (12) into the N-Boc-protected 5-azaspiro[2.4]heptane-6-carboxylic acid (1), a key element in the industrial synthesis of antiviral ledipasvir. Full article
(This article belongs to the Special Issue Advances in Stereoselective Synthesis)
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Review

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23 pages, 6057 KiB  
Review
Denitrative Cross-Couplings of Nitrostyrenes
by Michaela Marčeková, Branislav Ferko, Katarína Ráchel Detková and Pavol Jakubec
Molecules 2020, 25(15), 3390; https://doi.org/10.3390/molecules25153390 - 27 Jul 2020
Cited by 13 | Viewed by 3329
Abstract
Interestingly, β-nitrostyrenes, typically bench stable compounds, are highly promising cross-coupling partners, due to their excellent availability and well understood reactivity. In this review, we report on the discovery and advancements, in the field of stereoselective, denitrative cross-couplings of β-nitrostyrenes with miscellaneous organic reagents. [...] Read more.
Interestingly, β-nitrostyrenes, typically bench stable compounds, are highly promising cross-coupling partners, due to their excellent availability and well understood reactivity. In this review, we report on the discovery and advancements, in the field of stereoselective, denitrative cross-couplings of β-nitrostyrenes with miscellaneous organic reagents. The rapidly expanding field offers alternative access to a broad range of functionalized alkenes, including β-alkylated styrenes, chalcones, stilbenes, cinnamic acids, and conjugated sulfones and phosphonates. The most important mechanistic pathways are briefly discussed, to familiarize readers with the elementary reactions occurring during the coupling. Full article
(This article belongs to the Special Issue Advances in Stereoselective Synthesis)
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