Online citations, reference lists, and bibliographies.
← Back to Search

Using Stereoelectronic Effects To Explain Selective Reactions Of 4-substituted Five-membered Ring Oxocarbenium Ions.

D. M. Smith, K. Woerpel
Published 2004 · Chemistry, Medicine

Save to my Library
Download PDF
Analyze on Scholarcy
Share
[reaction: see text] The utility of the inside attack model to predict and analyze the stereoselectivities of nucleophilic additions to complex five-membered ring oxocarbenium ions is demonstrated in a systematic study of C-4-substituted acetals.
This paper references
10.1021/JA993349Z
A Stereoelectronic Model To Explain the Highly Stereoselective Reactions of Nucleophiles with Five-Membered-Ring Oxocarbenium Ions
Catharine H. Larsen (1999)
10.1002/1099-0690(200012)2000:23<3893::AID-EJOC3893>3.0.CO;2-E
On the Stereoselectivity of γ‐Lactol Substitutions with Allyl‐ and Propargylsilanes − Synthesis of Disubstituted Tetrahydrofuran Derivatives
A. Schmitt (2000)
10.1021/JO00294A047
An improved one-pot method for the stereoselective synthesis of the (2S,3R)-3-amino-2-hydroxy acids: key intermediates for bestatin and amastatin
R. Herranz (1990)
10.1021/JO970212N
Replicative Chirons: Stereoselective Synthesis of Oligo-Tetrahydrofuranic Lactones via C-Glycosylation with [(Trimethylsilyl)oxy]furan
B. Figadère (1997)
10.1021/JA038216Z
Total syntheses of amphidinolide T1, T3, T4, and T5.
C. Aïssa (2003)
10.1021/JA021385J
Enantioselective total synthesis of (+)-amphidinolide t1.
A. Ghosh (2003)
10.1021/BI010499P
Ricin A-chain inhibitors resembling the oxacarbenium ion transition state.
K. Tanaka (2001)
10.1016/S0040-4020(99)00441-X
Divergent diastereoselectivity in the addition of nucleophiles to tetrahydrofuran-derived oxonium ions
J. Shaw (1999)
10.1016/S0040-4020(01)00035-7
Vinylogous Mannich reactions: selectivity and synthetic utility
S. K. Bur (2001)
10.1063/1.473993
The torsional conformations of butane: Definitive energetics from ab initio methods
N. L. Allinger (1997)
10.1021/JA992750I
Ricin A-Chain: Kinetic Isotope Effects and Transition State Structure with Stem-Loop RNA†
Xiangyang Chen (2000)
10.1016/S1367-5931(01)00265-4
Chemistry and biology of arabinofuranosyl- and galactofuranosyl-containing polysaccharides.
J. Houseknecht (2001)
10.1021/JA00754A036
Characterization of torsional angle effects as the dominant steric effect in the hydroxymercuration of substituted cyclohexenes
D. Pasto (1971)
10.1126/SCIENCE.3945819
Theory and modeling of stereoselective organic reactions.
K. Houk (1986)
10.1021/JA037935A
Stereochemistry of nucleophilic substitution reactions depending upon substituent: evidence for electrostatic stabilization of pseudoaxial conformers of oxocarbenium ions by heteroatom substituents.
Leticia Ayala (2003)
10.1021/JA974003W
Determination of the Nucleophilicities of Silyl and Alkyl Enol Ethers
J. Burfeindt (1998)
10.1021/JO00071A031
Studies on the synthesis of cyanomethyleneamino pseudopeptides
R. Herranz (1993)
10.1055/S-1996-4162
Synthesis of Enantiopure 1,2-Didehydropyrrolidine, D-Proline, and Oxazoline Derivatives via Staudinger-Aza-Wittig Cyclization of γ-Azido Aldehydes
J. Mulzer (1996)
10.1039/B109930M
Access to 2,5-disubstituted tetrahydrofurans from Grignard reagents and hemiacetal derivatives.
X. Franck (2002)
10.1021/JA039716V
Synthesis of amphidinolide T1 via catalytic, stereoselective macrocyclization.
Elizabeth A. Colby (2004)
10.1002/1521-3765(20020902)8:17<3976::AID-CHEM3976>3.0.CO;2-7
Synthesis and conformational analysis of fructose-derived scaffolds: molecular diversity from a single molecule.
L. Cipolla (2002)
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)
10.1021/JO010823M
Diastereoselective nucleophilic substitution reactions of oxasilacyclopentane acetals: application of the "inside attack" model for reactions of five-membered ring oxocarbenium ions.
Teresa J. Bear (2002)
10.1021/BI027014X
Powering DNA repair through substrate electrostatic interactions.
Y. Jiang (2003)
10.1021/CR00054A001
Effect of conformational change on reactivity in organic chemistry. Evaluations, applications, and extensions of Curtin-Hammett Winstein-Holness kinetics
J. I. Seeman (1983)
10.1021/JO9709312
Stereoselective Synthesis of 2,2,5-Trisubstituted Tetrahydrofurans via the Lewis Acid-Assisted Reaction of Cyclic Hemiketals with Nucleophiles
Y. Nishiyama (1997)
10.1021/JO9713621
Stereocontrolled Total Synthesis of an Annonacin A-Type Acetogenin: Pseudoannonacin A?†
S. Hanessian (1998)
10.1021/OL005510C
Studies toward (-)-gymnodimine: concise routes to the spirocyclic and tetrahydrofuran moieties.
J. Yang (2000)



This paper is referenced by
10.1021/jo200639t
High 1,3-trans stereoselectivity in nucleophilic substitution at the anomeric position and β-fragmentation of the primary alkoxyl radical in 3-amino-3-deoxy-ribofuranose derivatives: application to the synthesis of 2-epi-(-)-jaspine B.
Alma Sánchez-Eleuterio (2011)
10.1039/b809570a
Stannyl ceramides as efficient acceptors for synthesising beta-galactosyl ceramides.
J. A. Morales-Serna (2008)
10.1021/OL061385E
Asymmetric total synthesis of (-)-panacene and correction of its relative configuration.
J. Boukouvalas (2006)
10.1021/jo400945j
Nucleophilic addition to silyl-protected five-membered ring oxocarbenium ions governed by stereoelectronic effects.
V. T. Tran (2013)
10.1021/ja104429y
Synthesis of 1',2'-cis-nucleoside analogues: evidence of stereoelectronic control for SN2 reactions at the anomeric center of furanosides.
M. Prévost (2010)
10.1002/EJOC.201301604
Short‐Step Anodic Access to Emissive RNA Homonucleosides
Yohei Okada (2014)
10.1021/acs.joc.7b01211
Stereocontrolled Nucleophilic Addition to Five-Membered Oxocarbenium Ions Directed by the Protecting Groups. Application to the Total Synthesis of (+)-Varitriol and of Two Diastereoisomers Thereof.
Alma Sánchez-Eleuterio (2017)
10.1002/EJOC.200701228
Direct and Efficient Glycosylation Protocol for Synthesizing α‐Glycolipids: Application to the Synthesis of KRN7000
Omar Boutureira (2008)
10.1039/B600056H
Electrostatic interactions in cations and their importance in biology and chemistry.
D. M. Smith (2006)
10.1016/B978-0-12-803739-3.00003-4
d- and l- altro - C -furanosides (II/ ent -II, α- C -Lyxose, α- C -Ribose)
Peter Goekjian (2017)
10.1007/S11426-010-4176-8
Two remarkable epimerizations imperative for the success of an asymmetric total synthesis of (+)-aigialospirol
R. Figueroa (2011)
10.1002/anie.201405477
Furanosyl oxocarbenium ion stability and stereoselectivity.
Erwin R van Rijssel (2014)
10.3987/COM-10-S(E)93
A Cyclic Acetal Tethered Intramolecular Diels-Alder Cycloaddition. Studies Directed toward a Total Synthesis of (±)-Fusidilactone C
R. P. Hsung (2010)
10.1016/J.TET.2008.10.087
Inverse stereoselectivity in the nucleophilic attack on five-membered ring oxocarbenium ions. Application to the total synthesis of 7-epi-(+)-goniofufurone
L. Hernandez-Garcia (2009)
10.1002/9783527696239.CH14
Selective Glycosylations with Furanosides
C. Gallo-Rodriguez (2017)
10.1016/J.TETLET.2005.08.082
A tandem C–H insertion—acetal cleavage sequence: stereocontrolled synthesis of substituted tetrahydrofurans
Amel Garbi (2005)
10.1016/J.TET.2016.01.003
Vinylsilane-mediated synthesis of styryl-lactone frameworks
S. Fearnley (2016)
10.1016/j.carres.2014.04.005
Stereoselective C-glycosidation of D-fucose derivatives directed by the protective groups.
Omar Cortezano-Arellano (2014)
10.1002/chem.201202639
Direct nucleophilic addition to N-alkoxyamides.
Yuta Yanagita (2013)
10.1021/ACSCATAL.7B00403
Brønsted Acid/Silane Catalytic System for Intramolecular Hydroalkoxylation and Hydroamination of Unactivated Alkynes
M. Shibuya (2017)
10.1016/J.TETLET.2006.09.023
Addition of carbon nucleophiles to cyclic N-acyliminium and oxocarbenium ions under solvent-free conditions
Luiz Antonio Fonseca de Godoy (2006)
10.1016/J.TET.2007.02.087
A versatile approach to pyrrolidine azasugars and homoazasugars based on a highly diastereoselective reductive benzyloxymethylation of protected tartarimide
X. Zhou (2007)
10.1016/j.carres.2009.03.025
A short and practical synthesis of two Hagen's gland lactones.
Evelyn Paz-Morales (2009)
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/acs.joc.5b00419
Stereoselectivity in the Lewis acid mediated reduction of ketofuranoses.
Erwin R van Rijssel (2015)
10.1016/B978-0-08-096805-6.00007-3
Five-Membered Ring Systems: Furans and Benzofurans
Zhihai Ke (2011)
10.1007/978-1-4614-8268-0_4
Conformations and Chemistry of Oxocarbenium Ion
M. Miljkovic̄ (2014)
10.1002/ADSC.201400630
Increasing the Reactivity of Amides towards Organometallic Reagents: An Overview
Vittorio Pace (2014)
10.1016/J.CARRES.2006.10.015
Nucleophilic substitution at the anomeric position of 1,2-O-isopropylidenefuranose derivatives. A novel stereoselective synthesis of cyclic phosphates analogous to cAMP.
M. Romero (2006)
10.1039/B615725D
An unusual stereoselectivity in the anomeric substitution with carbamates promoted by HNTf2.
Changhong Ko (2007)
10.1016/J.TETLET.2015.01.050
Trapping Hemiacetals with Phosphono Substituted Palladium π-Allyl Complexes for the Synthesis of Substituted Cyclic Ethers.
Nongnuch Sutivisedsak (2015)
Semantic Scholar Logo Some data provided by SemanticScholar