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Friday, April 24, 2020 | History

2 edition of Lewis acid-mediated ring expansion of methylenecyclopropanes. found in the catalog.

Lewis acid-mediated ring expansion of methylenecyclopropanes.

Mark Edward Scott

Lewis acid-mediated ring expansion of methylenecyclopropanes.

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Published .
Written in English


Edition Notes

ContributionsUniversity of Toronto. Dept. of Chemistry.
The Physical Object
Paginationx, 367 leaves :
Number of Pages367
ID Numbers
Open LibraryOL20893546M


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Lewis acid-mediated ring expansion of methylenecyclopropanes. by Mark Edward Scott Download PDF EPUB FB2

ChemInform Abstract: Lewis Acid-Mediated Highly Regioselective Ring-Expansion of Methyl 2-Phenyl(arylhydroxymethyl)cyclopropanecarboxylates Article in ChemInform 39(3) August Although they are highly strained, methylenecyclopropanes (MCPs) are readily accessible molecules that have served as useful building blocks in organic synthesis.

MCPs can undergo a variety of ring-opening reactions because the release of cyclopropyl ring strain (40 kcal/mol) can provide a thermodynamic driving force for reactions and the π-character of the bonds within the cyclopropane can Cited by: Treatment of methylenecyclopropanes (MCPs) with DIAD or DEAD in MeCN under mild conditions in the presence of Lewis acid Zr(OTf)4 gave the cyclobutanone ring-expansion products in good to high.

A novel synthetic route for the preparation of functionalized alkylidene pyrrolidines via a MAD/n-Bu4NI-mediated ring expansion of monoactivated MCP w Cited by: Brønsted acid-mediated ring-opening reactions of methylenecyclopropanes: a dramatic counter ion effect Li-Xiong Shao, Jin-Wen Huang, Min Shi Tetrahedron 60 (51), Cited by:   Lewis or Brønsted acid-mediated intramolecular rearrangement of VDCPs, () A facile access to medium- and large-size naphthalenacarbocycles via Lewis acid mediated ring-expansion reaction of bicyclic vinylidenecyclopropanes.

The Lewis acids catalyzed aza-Diels–Alder reaction of methylenecyclopropanes with : Lixiong Shao, Jianmei Lu, Min Shi.

Transition metal-catalyzed reactions of methylenecyclopropanes (MCPs) 1 have been widely explored in this area of study over the past decades. 1 The attractive feature of these compounds is their surprising stability along with a high level of strain.2, 3, 4 Strangely, less attention has been paid for the Lewis acid or Brønsted acid-mediated reactions of MCPs.

5 In the continuum of Lewis acid Cited by:   Shi M, Xu B, Huang JW () Lewis acid-mediated cycloaddition of methylenecyclopropanes with aldehydes and imines: a facile access to indene, THF, and pyrrolidine skeletons via homoallylic rearrangement protocol. Org Lett – Google ScholarCited by: 4.

the Lewis acid-mediated ring expansion of methylenecyclopropanes. He has been the recipient of an NSERC Postgraduate () Scholarship and an NSERC Postgraduate (Ph.D.) Scholarship. He will be pursuing his postdoctoral studies at Harvard University under the supervision of Prof.

David A. Evans following the completion of his Ph.D. Scheme File Size: 2MB. Enantioselective Lewis Acid Promoted Radical Cyclization I CO 2 c-Hex Lewis Acid Bu 3 SnH, Et 3 B CH 2 Cl 2, ˚ C CO 2 R H O RO s-trans LA First report of chiral Lewis Acid mediated radical cyclization Lewis Acid (Binol)AlMe equiv 1 ee (%) 2 SiPh 3 SiPh 3 O O Al Me 1 4 12 36 Reactions using the same Lewis Acid and the Weinreb amide provide File Size: KB.

Mg 35 Cu 24 Ga A Three‐Dimensional Cubic Network Composed of Interconnected Cu 6 Ga 6 Icosahedra, Mg‐Centered Ga 16 Icosioctahedra, and a Magnesium Lattice. Qisheng Lin; John D. Corbett; First Published: 09 March Inthey further published rapid generation of molecular complexity in the Lewis or Brønsted acid-mediated reactions of methylenecyclopropanes in Acc.

Chem. Res.45, As shown in Scheme 3, these Lewis or Brønsted acid-mediated reactions of MCPs can produce a variety of new compounds such as cyclobutanones, indenes. Our data suggests that a Lewis acid mechanism accounts for pyrrole formation (Scheme 2). In this mechanism, complexation of the Lewis acid to the α-nitrogen of the azide triggers an attack by the olefin to create the new C–N bond.

This mechanism appears mostly likely as electron-donating R-substituents accelerate the reaction. Scheme 2. A chemoselective synthesis of fused novel tricyclic motifs via a facile domino intramolecular cyclization is presented. The strategy enables the formation of dual C–C bond via intramolecular Friedel–Crafts alkylation followed by acylation to accomplish fused tricyclic ketones.

Significantly, these fused tricyclic compounds are ubiquitous and constitute major structural cores of natural Cited by: 4. A highly selective Lewis acid catalyzed annulation of three-membered heterocycles with nitrones has been developed. Oxiranes, aziridines, and thiiranes were used as substrates for the synthesis of various six-membered heterocycles using Al or In catalysts.

This catalytic protocol demonstrates a broad substrate scope and provides access to new structural motifs in high yields and in excellent.

Thieme E-Books & E-Journals. Biographical Sketches. David J. Aitken was born in and studied chemistry at the University of Strathclyde (Glasgow), obtaining his PhD inunder the supervision of Prof.

Wood and Prof. Suckling. After a two-year post-doctoral appointment with Prof. H.-P. Husson­ at the ICSN (Gif-sur-Yvette) he was appointed CNRS researcher at Descartes Cited by: Program Book. download Report.

Comments. Transcription. Program Book. You can write a book review and share your experiences. Other readers will always be interested in your opinion of the books you've read. Whether you've loved the book or not, if you give your honest and detailed thoughts then people will find new books that are right for them.

Free ebooks since Author Index Angew. Chem. Int. код для вставки ). Radicals in Organic Synthesis Edited by Philippe Renaud and Mukund P.

Sibi @WILEY-VCH Other Titles of Interest D. Curran, N. Porter, B. Giese Stereochemistry of Radical Reactions Concepts, Guidelines, and Synthetic Applications Diastereoselectivities in the tetrabutylammonium cyanide-catalysed cyanosilylation of cyclic α,β-epoxyketones are dependent on ring size, with a switchover in selectivity between five-membered and larger rings being explained through computation of TSs A range of Lewis bases catalyse the addition of TMSCN to aldehydes, with phosphines.

Lewis acid catalyzed ring-opening reactions of methylenecyclopropanes with diphenylphosphine oxide in the presence of sulfur or selenium. Min Shi,* Min Jiang and Le-Ping Liu, Org. Bio. Chem.5, 2. Reactions of methylenecyclobutanes with silver acetate and iodine. Min Jiang, Le-Ping Liu and Min Shi,* Tetrahedron.

63, Stereocontroll via σ-π chelation was achieved by using group 13 Lewis acids. During this study, we found that some palladium (II) species act not only as transition metal catalyst but also as Lewis acid catalyst.

Based on this finding, total syntheses of natural products, BCH and vibsanol, were achieved. Furthermore, antibiotics, (+)-ochromycinoneand (+)-rubiginone B2, were synthesized. All Journal Article Presentation Book Patent Solvent-Controlled Stereoselective Formation of a Cyclic Ether in the Lewis Acid-Mediated Allylation of an α-Chloroacetoxy Acyclic Ether.

A Novel Synthetic Method of Bicyclic Pyrans via the Palladium Catalyzed Tandem Cyclization/Ring Expansion between Enynals and Dimethyl Acetylene. Affiliation (based on the past Project Information):東北大学,原子分子材料科学高等研究機構,名誉教授, Research Field:物質変換,有機化学一般,Organic chemistry,Organic chemistry,Synthetic chemistry, Keywords:ルイス酸,不斉合成,中性子捕捉療法,アリルスズ,Asymmetric Synthesis,有機金属化合物,有機スズ化合物,立体選択的合成.

This banner text can have markup. web; books; video; audio; software; images; Toggle navigation. The first section of this thesis describes the development of an enantioselective synthesis of terminally unsubstituted methylenecyclopropanes. The key feature of this approach is a Rh2(STBPTTL) 4-mediated catalytic asymmetric cyclopropanation of unsubstituted allene to produce enantioenriched methylenecyclopropanes bearing alkyl or activated.

Coverage of the terminology appearing in JMLA was extended with terms from MeSH, NCI Thesaurus (NCI), Emtree, the HTA Database Canadian Repository [international repository for health technology assessment], and Robert Sandieson's synonym ring for research synthesis.

Collected terms were enriched with terms from the NCI Metathesaurus.