Unusual Formal [4 + 2] Cycloaddition of Ethyl Allenoate with Arylidenoxindoles: Synthesis of Dihydropyran-Fused Indoles
Organic LettersPublished 8 February 2011
Xiangyu Chen, Mingwei Wen, Song Ye, Zhixiang Wang
Citations65
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SJR score1.24
SNIP1.03
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TL;DR
An unusual DABCO-catalyzed formal cycloaddition of ethyl allenoate, as a surrogate of a "1,2-dipole", with various arylidenoxindoles has been developed for the synthesis of dihydropyran-fused indoles.
Abstract
An unusual DABCO-catalyzed formal [4 + 2] cycloaddition of ethyl allenoate, as a surrogate of a "1,2-dipole", with various arylidenoxindoles has been developed for the synthesis of dihydropyran-fused indoles. The DFT mechanistic study indicates that the cycloaddition takes place stepwise and the essential role of the catalyst is to raise the HOMO of allenoate.
Keywords
Chemistry
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Lewis base catalyzed reactions of N-Boc-imines and ethyl 2,3-butadienoate were investigated systematically and novel rearrangement product (E)-ethyl 2-((Z)-(tert-butoxycarbonylimino)(aryl)methyl)but-2-enoates could be formed in moderate yields.
Advanced Synthesis & CatalysisThe First Air‐Stable and Efficient Nucleophilic Trialkylphosphine Organocatalyst for the Baylis–Hillman Reaction
39 Citations2006Zhengrong He, Zhengrong He +4 more
Under the mediation of 15–20 mol % of PTA and practical conditions, both aromatic and aliphatic aldehydes react with the activated alkenes like acrylates and methyl vinyl ketone to afford the corresponding adducts in fair to excellent yields.
The Journal of Organic ChemistryInvestigation of an Organomagnesium-Based [3 + 3] Annelation to Pyrans and Its Application in the Synthesis of Rhopaloic Acid A
35 Citations2008Julien Brioche, Katharine M. Goodenough +2 more
A stepwise [3 + 3] annelation reaction has been developed that allows access to pyrans from epoxides and has been exemplified by its use in the preparation of rhopaloic acid A.
The Journal of Organic ChemistryTotally Regio- and Stereoselective Behavior of Mono- and Diactivated Cyclic Alkenes in the Lu Reaction: Synthesis of Enantiopure Functionalized Cyclopentanes
35 Citations2008J.L.G. Ruano, Alberto Núñez +2 more
5-Alkoxyfuran-2(5H)-ones and their optically pure 3-p-tolylsulfinyl derivatives, synthetic equivalents of the acyclic esters, react with dipoles generated from allenoates and PPh(3) (Lu reaction) in a completely regioselective, pi-facial selective and endo-selective manner, yielding bicyclic adducts.
Journal of the American Chemical SocietyKetene Acetals. XXXV. Cyclic Ketene Acetals and Orthoesters from 2,2-Dimethoxy-2,3-dihydropyran
32 Citations1955S. M. McElvain, Gordon R. McKay
The Journal of Organic ChemistryCation Radical Catalyzed Diels-Alder Reaction of Electron-Rich Allenes
31 Citations1995Michael Schmittel, C. Woehrle
Journal of the American Chemical SocietyBicyclic Dihydropyrans by the Diels-Alder Reaction
31 Citations1953William S. Emerson, Gail H. Birum +1 more
Angewandte Chemie International EditionSpecific Alkylation of Guanine Opposite to a Single Nucleotide Bulge: A Chemical Probe for the Bulged Structure of DNA
28 Citations1999Kazuhiko Nakatani, Akimitsu Okamoto +1 more
Remarkable enhancement of guanine alkylation just opposite a bulged site by 13R-1 compared with those in normal duplex DNA is ascribable to the formation of a unique intercalated complex that is attainable only at the bulged sites.
TetrahedronDomino routes to substituted benzoindolizines: tandem reorganization of 1,3-dipolar cycloadducts of nitrones with allenic esters/ketones and alternative cycloaddition–palladium catalyzed cyclization pathway
28 Citations2009Ashish Kapur, Kamal Kumar +7 more
European Journal of Organic ChemistryDiastereoselective Aza‐Baylis–Hillman Reactions: Synthesis of Chiral α‐Allenylamines and 2‐Azetines from Allenic Esters
25 Citations2010Bruna S. Santos, Ana L. Cardoso +5 more
Organic LettersDevelopment of a Stereoselective Co-Mediated Dihydropyran Ring Contraction
22 Citations2006Simon J. Meek, Fabienne Pradaux +2 more
A highly stereoselective approach for the synthesis of trans-1,2-disubstituted cyclobutanes through an Al-promoted cobalt-mediated O-->C ring contraction of dihydropyrans is described.
Tetrahedron LettersSynthesis and biological evaluation of a des-dihydropyran laulimalide analog
20 Citations2009Andreas Gollner, Karl‐Heinz Altmann +2 more
Chemical CommunicationsSwitching stereocontrol in the high pressure-induced hetero-Diels–Alder reaction
18 Citations2000Hashim Al‐Badri, Jacques Maddaluno +2 more
TetrahedronEnantioselective synthesis of functionalized 3,4-dihydropyran derivatives organocatalyzed by a novel fluorinated-diphenylprolinolether
17 Citations2009Chuanming Yu, Fei Zheng +2 more
MacromoleculesPolynucleotide analogs. 2. Synthesis, characterization, and physicochemical properties of alternating copolymers of dihydropyran-containing nucleic acid bases and maleic anhydride
12 Citations1992Man Jung Han, Choong Whan Lee +2 more
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