Author
Leo A. Paquette
Other affiliations: Heidelberg University
Bio: Leo A. Paquette is an academic researcher from Ohio State University. The author has contributed to research in topics: Ring (chemistry) & Total synthesis. The author has an hindex of 36, co-authored 484 publications receiving 6021 citations. Previous affiliations of Leo A. Paquette include Heidelberg University.
Topics: Ring (chemistry), Total synthesis, Ketone, Dodecahedrane, Isomerization
Papers published on a yearly basis
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TL;DR: In this paper, two examples of the title reaction are described, and the kinetically preferred pathway for 2 utilizes the vinyl substituent, while the variant for 16 skirts this option completely, and these biases are a function of the structural features inherent to these alochols.
Abstract: Two examples of the title reaction are described. While the kinetically preferred pathway for 2 utilizes the vinyl substituent, that for 16 skirts this option completely. To a great extent, these biases are a function of the structural features inherent to these alochols.
TL;DR: The feasibility of generating the anion of dodecahedrane by direct metalation, reductive lithiation with aromatic radical anions, and by transmetalation with alkyllithiums has been examined.
Abstract: The feasibility of generating the anion of dodecahedrane by direct metalation, by reductive lithiation with aromatic radical anions, and by transmetalation with alkyllithiums has been examined.
TL;DR: In this article, the first bands in the He(I) photoelectron spectra of "hypostrophene" (tetracyclo[5.3.0.02,6.2.03,10]deca-4,8-diene, 3) were analyzed.
Abstract: Analysis of the first bands in the He(I) photoelectron spectra of “hypostrophene” (tetracyclo[5.3.0.02,6.03,10]deca-4,8-diene, 3), its tetrahydro- (1), dihydro- (2), homo- (4), and bishomo-derivative (5) has been achieved on the basis of the correlations within the series 1 to 5 with accompanying semiempirical calculations of the MINDO/3 and SPINDO/1 type. The electronic structure of the first excited states of 3 and syn-tricyclo[4.2.0.02,5]octadiene is discussed in light of their inability to undergo [π2s + π2s] ring closure.
Orbital-Wechselwirkungen in „Hypostrophen”, seinen Hydro- und Homo-Derivaten. Eine photoelektronenspektroskopische Untersuchung
Die Analyse der ersten Banden in den He(I)-Photoelektronen(PE)-Spektren von „Hypostrophen” (Tetracyclo[5.3.0.02,6.03,10]deca-4,8-dien, 3) sowie seiner Tetrahydro- (1), Dihydro- (2), Homo-(4) und Bishomo-Derivate (5) beruht auf der Korrelation zwischen den Spektren von 1 bis 5 sowie dem Vergleich mit den Ergebnissen von semiempirischen Rechnungen vom MINDO/3 und SPINDO/1-Typ. Die Elektronenstruktur des ersten angeregten Zustands von 3 und syn-Tricyclo[4.2.0.02,5]octadien wird im Zusammenhang mit dem Ausbleiben einer [π2s + π2s]- Reaktion diskutiert.
TL;DR: In this paper, the reversibility of the thermal oxy-Cope rearrangement is demonstrated with the specific example, and the pathway and energetics associated with this phenomenon are outlined.
Abstract: The reversibility of the thermal oxy-Cope rearrangement is demonstrated with the specific example , and the pathway and energetics associated with this phenomenon are outlined.
TL;DR: In this article, the lithiation of (29) and (30) is shown to occur at all three sites with a dissimilar kinetic preference, and a convenient means has been developed for elaboration of the tricyclic eastern sector of the austa- lide mycotoxins.
Abstract: The lithiation of (29) and (30) is shown to occur at all three sites with a dissimilar kinetic preference. For the dihydrofuran, reaction at the proton labeled H β' operates predominantly; in the dihydropyran example, H α is the favored site of deprotonation. These protons repre- sent those that are the most deshielded in the respective 1 H NMR spec- tra. The same is true for (9) and (19), both of which undergo mediation adjacent to the ring oxygen. No crossover in regioselectivity is obser- ved, presumably because the methoxy substituent is sterically precluded from rotating freely. Mixed complexes (dimers, etc.) or mixed aggregates in low equilibrium concentration are key to understanding the acidifi- cation phenomenon of ortho hydrogens. As a consequence of the dominance of regiocontrol by the ring oxygen in (9), a convenient means has been developed for elaboration of the tricyclic eastern sector of the austa- lide mycotoxins
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TL;DR: This review covers the literature published in 2014 for marine natural products, with 1116 citations referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms.
4,649 citations
TL;DR: This Review provides an overview of C-H bond functionalization strategies for the rapid synthesis of biologically active compounds such as natural products and pharmaceutical targets.
Abstract: The direct functionalization of C-H bonds in organic compounds has recently emerged as a powerful and ideal method for the formation of carbon-carbon and carbon-heteroatom bonds. This Review provides an overview of C-H bond functionalization strategies for the rapid synthesis of biologically active compounds such as natural products and pharmaceutical targets.
2,391 citations
TL;DR: In this Review, highlights of a number of selected syntheses are discussed, demonstrating the enormous power of these processes in the art of total synthesis and underscore their future potential in chemical synthesis.
Abstract: In studying the evolution of organic chemistry and grasping its essence, one comes quickly to the conclusion that no other type of reaction plays as large a role in shaping this domain of science than carbon-carbon bond-forming reactions. The Grignard, Diels-Alder, and Wittig reactions are but three prominent examples of such processes, and are among those which have undeniably exercised decisive roles in the last century in the emergence of chemical synthesis as we know it today. In the last quarter of the 20th century, a new family of carbon-carbon bond-forming reactions based on transition-metal catalysts evolved as powerful tools in synthesis. Among them, the palladium-catalyzed cross-coupling reactions are the most prominent. In this Review, highlights of a number of selected syntheses are discussed. The examples chosen demonstrate the enormous power of these processes in the art of total synthesis and underscore their future potential in chemical synthesis.
2,268 citations
TL;DR: Reaction of R,â-Unsaturated Carbonyl Compounds 3127: Reaction of R-UnSaturated Carbonies 3127 7.1.6.
Abstract: 4.2.8. Reductive Coupling 3109 5. Reaction of Aromatic Compounds 3110 5.1. Electrophilic Substitutions 3110 5.2. Radical Substitution 3111 5.3. Oxidative Coupling 3111 5.4. Photochemical Reactions 3111 6. Reaction of Carbonyl Compounds 3111 6.1. Nucleophilic Additions 3111 6.1.1. Allylation 3111 6.1.2. Propargylation 3120 6.1.3. Benzylation 3121 6.1.4. Arylation/Vinylation 3121 6.1.5. Alkynylation 3121 6.1.6. Alkylation 3121 6.1.7. Reformatsky-Type Reaction 3122 6.1.8. Direct Aldol Reaction 3122 6.1.9. Mukaiyama Aldol Reaction 3124 6.1.10. Hydrogen Cyanide Addition 3125 6.2. Pinacol Coupling 3126 6.3. Wittig Reactions 3126 7. Reaction of R,â-Unsaturated Carbonyl Compounds 3127
2,031 citations
TL;DR: The power of cascade reactions in total synthesis is illustrated in the construction of complex molecules and underscore their future potential in chemical synthesis.
Abstract: The design and implementation of cascade reactions is a challenging facet of organic chemistry, yet one that can impart striking novelty, elegance, and efficiency to synthetic strategies. The application of cascade reactions to natural products synthesis represents a particularly demanding task, but the results can be both stunning and instructive. This Review highlights selected examples of cascade reactions in total synthesis, with particular emphasis on recent applications therein. The examples discussed herein illustrate the power of these processes in the construction of complex molecules and underscore their future potential in chemical synthesis.
1,762 citations