Stereoselective synthesis using D-Glucose-based dienes

by W. H. Yuen

Publisher: UMIST in Manchester

Written in English
Published: Downloads: 757
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Edition Notes

StatementW.H. Yuen ; supervised by R.J. Stoodley..
ContributionsStoodley, R. J., Chemistry.
ID Numbers
Open LibraryOL16809905M

  Stereoselective Synthesis of Drugs and Natural Products features contributions from an international team of synthetic chemists and pharmaceutical and natural product researchers. These authors have reviewed the tremendous body of literature in the field in order to compile a set of reliable, tested, and proven methods alongside step-by-step. Compiling material from leading contributors into one cohesive resource, this practical resource on synthetic methodology, reaction mechanisms, and applications for medicinal chemistry and drug discovery explores strategy and interdisciplinary work, laboratory synthesis for natural products, the preparative aspects of stereoselective synthesis. This strategy using D-glucose-based silyloxy dienes was applied towards the enantioselective synthesis of known or unknown anthracyclinones or their precursors in the Stoodley group over a . Question: "Stereoselective Formal Hydroamidation Of Si-Substituted Arylacetylenes With DIBAL-H And Isocyanates: Synthesis Of (E)- And (Z)-a-Silyl-a, B-unsaturated Amides" Lee, H.; Cho, S.; Lee, Y.; Jung, B. J. Org. Chem., ASAP. "Stereoisomerically Pure Trisubstituted Vinylaluminum Reagents And Their Utility In Copper-Catalyzed Enantioselective Synthesis Of 1,4-Dienes.

Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 31a. Arene-X (X=Hal, O, S, Se, Te) Stereoselective Synthesis 1. Stereoselective Reactions of Carbon–Carbon Double Bonds Stereoselective Synthesis 2. Stereoselective Reactions of Carbonyl and Imino Groups.   Overall, we have described a new stereoselective cross-coupling reaction between allylic alcohols and alkynes for the synthesis of 1,4-dienes. While occuring with allylic transposition, high stereoselectivity in the generation of substituted olefins is observed in coupling reactions with cyclic, as well as acyclic allylic alcohols. “Lewis-Acid Promoted Hetero [2 + 2] Cycloaddition Reactions of Aldehydes with Propynyl(10H)-acridone. A Highly Stereoselective Synthesis of Acrylic Acid Derivatives and 1,3-Dienes Using An Electron Deficient Variant of Ynamine.”. Conclusion: It can be seen from the review that the work done on this topic has employed the use of many different transition metal catalysts to perform various cycloadditions, cyclizations, and couplings using alkynyl halides. The reactions involving alkynyl halides were efficient in generating both carbon-carbon and carbonheteroatom bonds.

  Previous studies in our laboratory established that Ni-catalyzed 1,4-hydroboration of 1,3-dienes provides Z-alkenes with excellent control over the olefin geometry (> Z:E). 9,10 Application of this process to the construction of discodermolide requires the reaction of prochiral diene substrates such as in A (Figure 2).A critical question thus arises as to the influence of neighboring. Contents. Introduction to Dienamine Chemistry-- Synthesis and Applications of Preformed Dienamines-- Barbas Dienamines (2-Aminobuta-1,3-dienes): Scope and Applications-- Ramachary's Dienamines (Push-Pull Dienamines): In Situ Generation and Applications-- Serebryakov-Jorgensen Dienamines (1-Aminobuta-1,3-dienes): Different In Situ Generation Methods and Applications in [4+2]-Cycloadditions.

Stereoselective synthesis using D-Glucose-based dienes by W. H. Yuen Download PDF EPUB FB2

Monosaccharides, such as d-glucose are used as chiral auxiliaries in organic synthesis (Tadano and Totani, ) and in this study it is attached to silyloxy ing Stoodley's chromatography-free synthesis of (+)demethoxydaunomycinone (the aglycone of idarubicin) (Gupta et al., ), it was decided to follow a similar approach using a d-glucose-based silyloxy diene, based Cited by: 7.

A stereoselective synthesis of dienes and trienes is described via Na (Hg) reductive elimination of 1,4-dibenzoatealkenes and of 1,6-dibenzoate-2,4-dienes respectively. The reductive coupling of alkynes represents a powerful strategy for the rapid synthesis of highly substituted 1,3-dienes.

This method has the advantages of high atom and step economy, and readily available substrates. Unfortunately, the intermolecular coupling of.

An efficient aryl to vinyl 1,4‐palladium migration/Heck sequence was developed for the stereoselective synthesis of 1,3‐dienes. High stereoselectivity was observed not only for 1,3‐dienes bearing two similar aryl groups at terminal positions, but also for those with configurations shown to be unfavorable with previous by:   A new method for the stereoselective synthesis of dienes from aldehydes and N-allylhydrazine derivatives has been developed.

High levels of (E)-stereoselectivity are obtained for a variety of substrates. Addition of a dienophile to the reaction mixture allows a one-flask diene synthesis−cycloaddition by: Journals & Books; Help Download full text in PDF Download. Advanced. Tetrahedron Letters.

Vol Issue 2, 8 JanuaryPages Stereoselective intramolecular enone-olefin photocycloadditions of 1,7-dienes: Model studies on the synthesis of lycopodium alkaloids.

Written by a well-respected and experienced author, this textbook fills the gap for a concise introduction to the key concepts of organic stereochemistry and the most important classical and modern methods in stereoselective synthesis.

The concepts are extensively illustrated in color, with practical examples and question-answer sets to help consolidate the readers knowledge. Different substrates will be considered, ranging from silylated conjugated dienes, enynes, polyenynes, diynes and polyynes.

All these compounds represent versatile building blocks in the organic synthesis, as demonstred from the numerous applications, regarding especially the stereoselective synthesis of natural products with a conjugated.

Two complementary regiodivergent [(P,N)Ni]-catalyzed hydroalkylations of branched dienes are reported. When amides are employed as unstabilized C(sp3) nucleophiles, a highly regioselective 1,4-addition process is favored.

The addition products are obtained in high yield and with excellent stereocontrol of the internal olefin. With use of a chiral ligand and imides as carbon nucleophiles, a 3,4.

Stereoselective Polymerization with Single-Site Catalysts book. Elastomeric Homo-Polypropylene: Solid State Properties and Synthesis via Control of Reaction Parameters.

With Sabine Hild, Cecilia Cobzaru, Carsten Troll, Bernhard Rieger. Regioselective anti-allylindation of alkynes was achieved using InBr3 and allylic silanes.

Various types of alkynes and allylic silanes were applicable to the present allylindation. This sequential process used the generated 1,4-dienylindiums to establish novel synthetic methods for skipped dienes.

The 1,4-dienylindiums were characterized by spectral analysis and treated with I2 to. Stereoselective Synthesis of Difunctionalized 1,3-Dienes Containing Silicon and Selenium via in good yields.

(1E,3Z)Arylseleno(trimethylsilyl)-substituted 1,3-dienes 5 could be synthesized stereoselectively via hydrozirconation of (Z)(trimethylsilyl Books; Keep up to date. Register to receive personalised research and resources.

The efficient and stereoselective synthesis of polysubstituted butadienes, especially the multifunctional butadienes, represents a great challenge in organic synthesis.

Herein, we wish to report a distinctive Pd(0) carbene-initiated decarboxylative olefination approach that enables the direct coupling of diazo esters with vinylethylene carbonates (VECs), vinyl oxazolidinones, or vinyl. Iron catalyzed stereoselective alkene synthesis: a sustainable pathway including carbohalogenation, hydro/carbometalation of alkynes (allenes and dienes), alkylation and arylation of stereodefined (pseudo) haloalkenes or alkenyl metals, chelation-assisted C–H activation and other miscellaneous reactions.

books or book chapters) do not. Abstract. The cobalt catalyzed neutral Diels-Alder reaction of various acyclic 1,3-dienes and norbornadiene with 1,3-diynes can be controlled to give the adduct, whereas the adducts are only formed with sterically less hindered 1,3-dienes.

A stereoselective approach towards ethyl-substituted conjugated dienoic esters utilising a Suzuki cross-coupling reaction has been achieved. In addition, a method for their conversion into the corresponding ethyl ketones is presented. Keck, T. Muller, S. Bräse, Synlett,  This strategy using d -glucose-based silyloxy dienes was applied towards the enantioselective synthesis of known or unknown anthracyclinones or their precursors in the Stoodley group over a period of ca.

20 years with some of these reported in the literature ((+)-daunomycinone 44 (Edwards et al., ), (+)demethoxy-1,4-dimethyldaunomycinone 45 (Kotha and Stoodley, ). Catalytic, stereoselective synthesis of skipped dienes is an important topic in organic synthesis.

Summarized here are the transition-metal-catalyzed stereoselective approaches and a new, photoinduced stereodivergent strategy reported by our group recently. Journals & Books; Register Sign in. Vol IsPages Direct, stereoselective synthesis of either E - or Z-1,3-dienes.

Author links open overlay panel Junzo Ukai Yoshihiko Ikeda Nobuo Ikeda Hisashi Yamamoto. Stereoselective synthesis of cis-2,6-bis-hydroxyalkyl-tetrahydropyrans by the permanganate promoted oxidative cyclisation of 1,6-dienes.

Tetrahedron Letters45 (39), Jiawang Liu, Ji Yang, Wolfgang Baumann, Ralf Jackstell, Matthias Beller, Stereoselective Synthesis of Highly Substituted Conjugated Dienes via Pd‐Catalyzed Carbonylation of 1,3‐Diynes, Angewandte Chemie International Edition, /anie, 58, 31, (), ().

Synthesis of 1,3-diene from alkyne and ethylene (1 atm) was improved using a ruthenium NHC carbene complex having a heterocyclic carbene as a ligand. Various 1,3-dienes could be synthesized from alkynes and ethylene.

Tonogakia, M. Mori, Tetrahedron Lett.,43, Enantioselective synthesis, also called asymmetric synthesis, is a form of chemical synthesis.

It is defined by IUPAC as: a chemical reaction (or reaction sequence) in which one or more new elements of chirality are formed in a substrate molecule and which produces the stereoisomeric (enantiomeric or diastereoisomeric) products in unequal amounts.

Put more simply: it is the synthesis of a. see article for more reactions. Abstract. A stereoselective synthesis of dienes from aldehydes and N-allylhydrazine derivatives offers high levels of (E)-stereoselectivity for a variety of on of a dienophile to the reaction mixture allows a one-flask diene synthesis-cycloaddition sequence.

The stereoselective synthesis of conjugated dienes was realized for the first time via Pd‐catalyzed alkoxycarbonylation of easily available 1,3‐diynes. Key to success is the utilization of the specific ligand 1,1′‐ferrocenediyl‐bis(tert‐butyl(pyridin‐2‐yl)phosphine) (L1), which allows this novel transformation to proceed at.

Recent Advances in Stereoselective Synthesis of 1,3-Dienes. Hu X. Peter Zhang Selective Olefination of Carbonyl Compounds via Metal-Catalyzed Carbene Transfer from Diazo Reagents.

Lei H. Li Selective Alkene Metathesis in the Total Synthesis of Complex Natural Product. Gu S.-K. Tian Olefination Reactions of Phosphorus-Stabilized Carbon. The desymmetrization of symmetric compounds is a useful approach to obtain chiral building blocks. Readily available precursors with a prochiral unit could be converted into complex molecules with multiple stereogenic centers in a single step.

In this review, recent advances in the desymmetrization of symmetric dienes in the diastereotopic group differentiating reaction and its synthetic. A novel palladium-catalyzed regio- and stereoselective dienylation via a combination of cascade carbopalladation and subsequent desulfitative coupling after the base-induced ring opening of sulfolenes has been described.

In this reaction, a range of Z-selective conjugated dienes bearing oxindoles or isoquinolinediones are obtained in moderate yields. This website applies cookies. Cookies are text snippets sent to your browser in order to provide you with a better user experience.

When visiting this website next time, the system will get back information on your previous session and facilitate navigation. Synthesis of N-Heterocycles via Iminyl Radicals.

John Walton and co-workers from the University of St. Andrews, UK, have reported on the use of O-phenyl oxime ethers as precursors for iminyl radicals en route for N-heterocycle synthesis (J. Org. Chem.73, Microwave irradiation was employed for the thermolysis of functionalized O-phenyl oximes 1 generating the iminyl radicals 2.

–Alder reactions using D-glucose-based silyloxy dienes General scope Monosaccharides such as D-glucose are used as chiral auxiliaries in organic synthesis (Tadano and Totani, ). Stereoselective Synthesis of Borylated 1,3-Dienes by Synergistic Cu/Pd Catalysis.

ChemCatChem10 (21), DOI: /cctc Andrew Whyte, Katherine I. Burton, Jingli Zhang, Mark Lautens. Enantioselective Intramolecular Copper‐Catalyzed Borylacylation.A convenient methodology for the highly stereoselective synthesis of unsymmetrical (1E,3E)-1,4-disubstituted 1,3-dienes based on palladium-catalyzed Hiyama cross-coupling reaction of 1-(triethoxysilyl)-substituted buta-1,3-dienes with aryl iodides is reported.