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Heterocycle Synthesis Based On Allylic Alcohol Transposition Using Traceless Trapping Groups.

Youwei Xie, P. Floreancig
Published 2014 · Chemistry, Medicine

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Allylic alcohols undergo transposition reactions in the presence of Re2 O7 whereby the equilibrium can be dictated by trapping one isomer with a pendent electrophile. Additional ionization can occur when the trapping group is an aldehyde or ketone, thus leading to cyclic oxocarbenium ion formation. Terminating the process through bimolecular nucleophilic addition into the intermediate provides a versatile method for the synthesis of diverse oxygen-containing heterocycles. Understanding the relative rates of the steps in the sequence leads to the design of reactions which create multiple stereocenters with good to excellent levels of control.
This paper references
10.1002/anie.201208132
Cascade approach to stereoselective polycyclic ether formation: epoxides as trapping agents in the transposition of allylic alcohols.
Youwei Xie (2013)
10.1002/ANIE.199709761
MECHANISTIC INSIGHTS INTO THE VERY EFFICIENT REO3OSIR3-CATALYZED ISOMERIZATION OF ALLYL ALCOHOLS
S. Bellemin-Laponnaz (1997)
10.1002/ANGE.200900600
Epoxidöffnungskaskaden zur Synthese polycyclischer Polyether-Naturstoffe
I. Vilotijevic (2009)
10.1021/JO00412A030
Synthetic applications of cyclic .alpha.-chloro ethers and thioethers. 4. Use of (thio)acetal esters as reagents for the protection of alcohols. Synthesis of 2-tetrahydrothienyl ethers
C. Kruse (1978)
10.1021/JA0375176
Nucleophilic additions to fused bicyclic five-membered ring oxocarbenium ions: evidence for preferential attack on the inside face.
D. M. Smith (2003)
10.1002/anie.201001681
Total synthesis of (-)-dactylolide.
S. Yun (2010)
10.1021/JA036439J
Stereoselective construction of cyclic ethers using a tandem two-component etherification: elucidation of the role of bismuth tribromide.
P. Evans (2003)
10.1039/C1SC00570G
Stereoselective heterocycle synthesis through a reversible allylic alcohol transposition and nucleophilic addition sequence
Youwei Xie (2011)
10.1002/cctc.200900206
Perrhenate Esters in New Catalytic Reactions
S. Bellemin-Laponnaz (2009)
10.1021/JA0620639
Regiochemical control in the metal-catalyzed transposition of allylic silyl ethers.
E. Hansen (2006)
10.1002/chem.201202839
Towards a comprehensive hydride donor ability scale.
M. Horn (2013)
10.1021/OL035438T
Stereoselective construction of cis-2,6-disubstituted tetrahydropyrans via the reductive etherification of delta-trialkylsilyloxy substituted ketones: total synthesis of (-)-centrolobine.
P. Evans (2003)
10.1002/chem.201102899
Total synthesis of laulimalide: assembly of the fragments and completion of the synthesis of the natural product and a potent analogue.
B. Trost (2012)
10.1021/OL061072J
Approach to the synthesis of cladiell-11-ene-3,6,7-triol.
John M. Hutchison (2006)
10.1002/ANIE.200702999
Oxidative cleavage in the construction of complex molecules: synthesis of the leucascandrolide A macrolactone.
H. H. Jung (2007)
10.1016/S0040-4020(01)88874-8
Rearrangement of Allylic and Propargylic Alcohols Catalyzed by the Combined Use of tetrabutylammonium perrhenate (VII) and p-toluenesulfonic acid
K. Narasaka (1992)
10.1126/science.1182826
Asymmetric Cooperative Catalysis of Strong Brønsted Acid–Promoted Reactions Using Chiral Ureas
H. Xu (2010)
10.3762/bjoc.9.174
Re2O7-catalyzed reaction of hemiacetals and aldehydes with O-, S-, and C-nucleophiles
W. Sittiwong (2013)
10.1021/JA993349Z
A Stereoelectronic Model To Explain the Highly Stereoselective Reactions of Nucleophiles with Five-Membered-Ring Oxocarbenium Ions
Catharine H. Larsen (1999)
10.1021/JA002231B
Enantioselective Total Synthesis of (−)-Galanthamine
B. M. T. and (2000)
10.1016/J.TETLET.2009.09.129
New Architectures in Hydrogen Bond Catalysis.
Andrew Rodriguez (2009)
10.1021/ja101673v
Regio- and stereocontrol in rhenium-catalyzed transposition of allylic alcohols.
Aaron T. Herrmann (2010)
10.1002/anie.201307133
Thiophosphoramide-based cooperative catalysts for Brønsted acid promoted ionic Diels-Alder reactions.
Alina Borovika (2013)
10.1021/ol801859c
Mild and efficient Re(VII)-catalyzed synthesis of 1,1-dihydroperoxides.
P. Ghorai (2008)
10.1002/anie.200802548
Total synthesis of theopederin D.
M. E. Green (2008)
10.1039/c2cc38198b
Anion recognition and transport properties of sulfamide-, phosphoric triamide- and thiophosphoric triamide-based receptors.
Philippa B. Cranwell (2013)
10.1021/CR0509758
Potassium organotrifluoroborates: new perspectives in organic synthesis.
Sylvain Darses (2008)
10.1016/J.TET.2005.09.045
BiBr3 initiated cyclization–addition reactions: effect of π-nucleophile on oxocarbenium ion addition and total syntheses of (+)-(S,S)-(cis-6-methyltetrahydropyran-2-yl)acetic acid and its trans-diastereomer
R. Hinkle (2005)
10.1002/ANGE.19971090915
MECHANISTISCHE EINBLICKE IN DIE HOCHEFFIZIENTE, REO3(OSIR3)-KATALYSIERTE ISOMERISIERUNG VON ALLYLALKOHOLEN
S. Bellemin-Laponnaz (1997)
10.1021/JA00382A053
Highly stereoselective approaches to .alpha.- and .beta.-C-glycopyranosides
M. D. Lewis (1982)
10.1002/anie.200900600
Epoxide-opening cascades in the synthesis of polycyclic polyether natural products.
I. Vilotijevic (2009)
10.1021/JA0524043
Stereoselective C-glycosylation reactions of ribose derivatives: electronic effects of five-membered ring oxocarbenium ions.
Catharine H. Larsen (2005)



This paper is referenced by
10.1016/B978-0-08-099406-2.00016-9
Chapter 5.4 – Six-Membered Ring Systems: With O and/or S Atoms
Clementina M M Santos (2013)
10.1002/chem.201600248
Mutual Cooperation in the Formal Allyl Alcohol Nucleophilic Substitution and Hydration of Alkynes for the Construction of γ-Substituted Ketones.
K. Huang (2016)
10.1021/acs.joc.7b01181
Modular Construction of Protected 1,2/1,3-Diols, -Amino Alcohols, and -Diamines via Catalytic Asymmetric Dehydrative Allylation: An Application to Synthesis of Sphingosine.
S. Tanaka (2017)
10.1016/B978-0-08-100017-5.00015-7
Six-Membered Ring Systems: With O and/or S Atoms
Clementina M M Santos (2014)
10.1002/anie.201916270
Dictating Thermodynamic Control through Tethering: Applications to Stereoselective Bis-Spiroketal Synthesis.
P. Floreancig (2020)
10.1002/anie.201705924
Re2 O7 -Mediated Dehydrative Cyclization Reactions: Total Synthesis of Herboxidiene and Its 12-Desmethyl Analogue.
Tyler M Rohrs (2017)
10.1002/anie.201808937
Total Synthesis of Putative Chagosensine.
M. Heinrich (2018)
10.1021/ol502633j
A concise and unified strategy for synthesis of the C1-C18 macrolactone fragments of FD-891, FD-892 and their analogues: formal total synthesis of FD-891.
N. Kanoh (2014)
10.1002/CHIN.201442030
Heterocycle Synthesis Based on Allylic Alcohol Transposition Using Traceless Trapping Groups.
Youwei Xie (2014)
10.1016/J.TET.2016.06.076
Recent advances in the synthesis of tetrahydrofurans and applications in total synthesis
A. D. L. Torre (2016)
10.1016/J.TETLET.2017.01.066
A Re2O7 catalyzed cycloetherification of monoallylic diols
Xiaolong Wan (2017)
10.1039/c4cc08604j
Thiophosphoramides as cooperative catalysts for copper-catalyzed arylation of carboxylates with diaryliodonium salts.
Bijay Bhattarai (2015)
10.1039/C6RA10399E
Tandem allylic alcohol isomerization/oxo-Michael addition reaction promoted by Re2O7
J. Hu (2016)
10.1039/c8sc03570a
Diarylmethane synthesis through Re2O7-catalyzed bimolecular dehydrative Friedel–Crafts reactions† †Electronic supplementary information (ESI) available: Experimental protocols and spectral data. See DOI: 10.1039/c8sc03570a
Q. Qin (2018)
10.1021/CS501618H
Acid- and Iridium-Catalyzed Tandem 1,3-Transposition/3,1-Hydrogen Shift/Chlorination of Allylic Alcohols
Ana Vázquez-Romero (2015)
10.1021/jacs.7b05832
Reductive Etherification via Anion-Binding Catalysis.
C. Zhao (2017)
10.1039/c4cc02826k
Enantioselective Prins cyclization: BINOL-derived phosphoric acid and CuCl synergistic catalysis.
C. Lalli (2014)
10.1002/SLCT.201601161
Synthesis of Medium‐Sized 2,ω‐cis‐Disubstituted Cyclic Ethers by Reductive Cyclization of Hydroxy Ketones
Gloria Hernández-Torres (2016)
10.1021/ACSCATAL.6B03651
Gold(I)-Catalyzed Enantioselective [2+2+2] Cycloadditions: An Expedient Entry to Enantioenriched Tetrahydropyran Scaffolds
I. Varela (2017)
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