scispace - formally typeset
Search or ask a question
Author

Daniel L. Comins

Bio: Daniel L. Comins is an academic researcher from North Carolina State University. The author has contributed to research in topics: Enantioselective synthesis & Chiral auxiliary. The author has an hindex of 47, co-authored 278 publications receiving 6465 citations. Previous affiliations of Daniel L. Comins include Utah State University & Eli Lilly and Company.


Papers
More filters
Journal ArticleDOI
TL;DR: In this paper, the enolates of ketones are trapped with an N-(2-pyridyl)triflimide at low temperatures to give vinyl triflates.

443 citations

Journal ArticleDOI
TL;DR: Grignard addition to a chiral 1-acyl-4-methoxypyridinium salt provides synthetically useful 2-alkyl(aryl)-2,3-dihydro-4 pyridones in high diastereomeric excess as discussed by the authors.
Abstract: Grignard addition to a chiral 1-acyl-4-methoxypyridinium salt provides synthetically useful 2-alkyl(aryl)-2,3-dihydro-4-pyridones in high diastereomeric excess

167 citations

Journal ArticleDOI
TL;DR: An anionic chiral auxiliary mediated asymmetric alkylation of carbamate 2 provides 3-substituted isoindolinones 4 in high ee in the first asymmetric synthesis of (+)-lennoxamine.

142 citations

Journal ArticleDOI
TL;DR: In this article, the dialkyl amidures de lithium sur des aldehydes aromatiques (naphtalenecarbaldehydes, benzene substitues) dans le THF ou le benzene, conduit a des hemiaminals qui sont lithies en position ortho par le butyl-lithium L'alkylation suivie de l'hydrolyse, des produits lithies fournit les arenals substitues en ortho
Abstract: L'addition de dialkyl amidures de lithium sur des aldehydes aromatiques (naphtalenecarbaldehydes, benzaldehydes substitues) dans le THF ou le benzene, conduit a des hemiaminals qui sont lithies en position ortho par le butyl-lithium L'alkylation suivie de l'hydrolyse, des produits lithies fournit les arenals substitues en ortho

137 citations


Cited by
More filters
Journal ArticleDOI
TL;DR: A number of improvements have developed the former process into an industrially very useful and attractive method for the construction of aryl -aryl bonds, but the need still exists for more efficient routes whereby the same outcome is accomplished, but with reduced waste and in fewer steps.
Abstract: The biaryl structural motif is a predominant feature in many pharmaceutically relevant and biologically active compounds. As a result, for over a century 1 organic chemists have sought to develop new and more efficient aryl -aryl bond-forming methods. Although there exist a variety of routes for the construction of aryl -aryl bonds, arguably the most common method is through the use of transition-metalmediated reactions. 2-4 While earlier reports focused on the use of stoichiometric quantities of a transition metal to carry out the desired transformation, modern methods of transitionmetal-catalyzed aryl -aryl coupling have focused on the development of high-yielding reactions achieved with excellent selectivity and high functional group tolerance under mild reaction conditions. Typically, these reactions involve either the coupling of an aryl halide or pseudohalide with an organometallic reagent (Scheme 1), or the homocoupling of two aryl halides or two organometallic reagents. Although a number of improvements have developed the former process into an industrially very useful and attractive method for the construction of aryl -aryl bonds, the need still exists for more efficient routes whereby the same outcome is accomplished, but with reduced waste and in fewer steps. In particular, the obligation to use coupling partners that are both activated is wasteful since it necessitates the installation and then subsequent disposal of stoichiometric activating agents. Furthermore, preparation of preactivated aryl substrates often requires several steps, which in itself can be a time-consuming and economically inefficient process.

3,204 citations

Journal ArticleDOI
TL;DR: Transition-Metal-Free Reactions, Alkynylation of Heterocycles, and Synthesis of Electronic and Electrooptical Molecules: A Review.
Abstract: 3.7. Palladium Nanoparticles as Catalysts 888 3.8. Other Transition-Metal Complexes 888 3.9. Transition-Metal-Free Reactions 889 4. Applications 889 4.1. Alkynylation of Arenes 889 4.2. Alkynylation of Heterocycles 891 4.3. Synthesis of Enynes and Enediynes 894 4.4. Synthesis of Ynones 896 4.5. Synthesis of Carbocyclic Systems 897 4.6. Synthesis of Heterocyclic Systems 898 4.7. Synthesis of Natural Products 903 4.8. Synthesis of Electronic and Electrooptical Molecules 906

2,522 citations

Journal ArticleDOI
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

Journal ArticleDOI
TL;DR: This review covers the isolation, structure determination, synthesis and biological activity of quinoline, quinazoline and acridone alkaloids from plant, microbial and animal sources.

1,687 citations

Journal ArticleDOI
TL;DR: The present review summarizes the data that appeared in the literature following publication of previous reviews in 1996 and 2002 and is organized according to the classes of organic polyvalent iodine compounds with emphasis on their synthetic application.
Abstract: Starting from the early 1990’s, the chemistry of polyvalent iodine organic compounds has experienced an explosive development. This surging interest in iodine compounds is mainly due to the very useful oxidizing properties of polyvalent organic iodine reagents, combined with their benign environmental character and commercial availability. Iodine(III) and iodine(V) derivatives are now routinely used in organic synthesis as reagents for various selective oxidative transformations of complex organic molecules. Several areas of hypervalent organoiodine chemistry have recently attracted especially active interest and research activity. These areas, in particular, include the synthetic applications of 2-iodoxybenzoic acid (IBX) and similar oxidizing reagents based on the iodine(V) derivatives, the development and synthetic use of polymer-supported and recyclable polyvalent iodine reagents, the catalytic applications of organoiodine compounds, and structural studies of complexes and supramolecular assemblies of polyvalent iodine compounds. The chemistry of polyvalent iodine has previously been covered in four books1–4 and several comprehensive review papers.5–17 Numerous reviews on specific classes of polyvalent iodine compounds and their synthetic applications have recently been published.18–61 Most notable are the specialized reviews on [hydroxy(tosyloxy)iodo]benzene,41 the chemistry and synthetic applications of iodonium salts,29,36,38,42,43,46,47,54,55 the chemistry of iodonium ylides,56–58 the chemistry of iminoiodanes,28 hypervalent iodine fluorides,27 electrophilic perfluoroalkylations,44 perfluoroorgano hypervalent iodine compounds,61 the chemistry of benziodoxoles,24,45 polymer-supported hypervalent iodine reagents,30 hypervalent iodine-mediated ring contraction reactions,21 application of hypervalent iodine in the synthesis of heterocycles,25,40 application of hypervalent iodine in the oxidation of phenolic compounds,32,34,50–53,60 oxidation of carbonyl compounds with organohypervalent iodine reagents,37 application of hypervalent iodine in (hetero)biaryl coupling reactions,31 phosphorolytic reactivity of o-iodosylcarboxylates,33 coordination of hypervalent iodine,19 transition metal catalyzed reactions of hypervalent iodine compounds,18 radical reactions of hypervalent iodine,35,39 stereoselective reactions of hypervalent iodine electrophiles,48 catalytic applications of organoiodine compounds,20,49 and synthetic applications of pentavalent iodine reagents.22,23,26,59 The main purpose of the present review is to summarize the data that appeared in the literature following publication of our previous reviews in 1996 and 2002. In addition, a brief introductory discussion of the most important earlier works is provided in each section. The review is organized according to the classes of organic polyvalent iodine compounds with emphasis on their synthetic application. Literature coverage is through July 2008.

1,518 citations