Table of Contents

February 17, 2006
Volume 71, Issue 4
Pages 1289-1754

About the Cover: There are relatively few families of molecules displaying large surfaces of preorganized concavity. Furthermore, patterning these generally highly symmetric surfaces with functionality can lead to many products, making this approach to enzyme mimicry problematic. One way to "beat the odds" is to use a functionalization strategy that is tied to the structure of the host. Thus, for the shown deep-cavity cavitand, directed ortho metallation with different alkyllithiums leads to only twelve products. The remainder of the sixty-nine possible products are not observed because the preorganization of the host disfavors intermediates with proximal anionic charges. See Laughrey and Gibb, p 1289. View the article.

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Articles

Directed Ortho Metallation of Deep Cavity Cavitands: Functionalizing Molecular Concavity

pp 1289–1294
Publication Date (Web): October 12, 2005 (Article)
DOI: 10.1021/jo0513515

N-Nitroso- and N-Nitraminotetrazoles

pp 1295–1305
Publication Date (Web): January 27, 2006 (Article)
DOI: 10.1021/jo0513820

Synthesis and Properties of Trans-3‘,4‘-Bridged Nucleic Acids Having Typical S-type Sugar Conformation

pp 1306–1316
Publication Date (Web): January 24, 2006 (Article)
DOI: 10.1021/jo051187l

Zn(pybox)-Complex-Catalyzed Asymmetric Aqueous Mukaiyama-Aldol Reactions

pp 1317–1321
Publication Date (Web): January 26, 2006 (Article)
DOI: 10.1021/jo0514568

An Improved Aldehyde Linker for the Solid Phase Synthesis of Hindered Amides

pp 1322–1329
Publication Date (Web): January 27, 2006 (Article)
DOI: 10.1021/jo051742j

Synthesis of Isoprostanyl Phosphatidylcholine and Isoprostanyl Phosphatidylethanolamine

pp 1330–1334
Publication Date (Web): January 17, 2006 (Article)
DOI: 10.1021/jo0518553

A Flexible Stereospecific Synthesis of Polyhydroxylated Pyrrolizidines from Commercially Available Pyranosides

pp 1335–1343
Publication Date (Web): January 17, 2006 (Article)
DOI: 10.1021/jo051792o

Substituent-Dependent Anomeric Effects as a Source of Conformational Preference in Pyridinium Methylides

pp 1344–1350
Publication Date (Web): January 17, 2006 (Article)
DOI: 10.1021/jo051852q

Facile Synthesis and Characterization of Naphthidines as a New Class of Highly Nonplanar Electron Donors Giving Robust Radical Cations

pp 1351–1361
Publication Date (Web): January 19, 2006 (Article)
DOI: 10.1021/jo0517444

Rigid Molecular Tripod with an Adamantane Framework and Thiol Legs. Synthesis and Observation of an Ordered Monolayer on Au(111)

pp 1362–1369
Publication Date (Web): January 20, 2006 (Article)
DOI: 10.1021/jo051863j

Total Synthesis of 8,12-iso-iPF3α-VI, an EPA-Derived Isoprostane: Stereoselective Introduction of the Fifth Asymmetric Center

pp 1370–1379
Publication Date (Web): January 24, 2006 (Article)
DOI: 10.1021/jo051916x

New Glycomimetics: Anomeric Sulfonates, Sulfenamides, and Sulfonamides

pp 1380–1389
Publication Date (Web): January 13, 2006 (Article)
DOI: 10.1021/jo0520386

Synthesis of a Nonavalent Mannoside Glycodendrimer Based on Pentaerythritol

pp 1390–1398
Publication Date (Web): January 21, 2006 (Article)
DOI: 10.1021/jo052045u

Synthesis of Azolyl Carboximidamides as Ligands for Zn(II) and Cu(II): Application of the Zn(II) Complexes as Catalysts for the Copolymerization of Carbon Dioxide and Epoxides1

pp 1399–1406
Publication Date (Web): January 17, 2006 (Article)
DOI: 10.1021/jo052056n

Unprecedented Lability of the 5‘-O-tert-Butyldimethylsilyl Group from 3‘-Spiro-5‘‘-(4‘‘-acylamino-1‘‘,2‘‘-oxathiole-2‘‘,2‘‘-dioxide) Nucleoside Derivatives via Neighboring Group Participation of the 4‘‘-Acylamino Residue

pp 1407–1415
Publication Date (Web): January 21, 2006 (Article)
DOI: 10.1021/jo0520588

Synthesis of the Proposed Structure of Mucoxin via Regio- and Stereoselective Tetrahydrofuran Ring-Forming Strategies

pp 1416–1429
Publication Date (Web): January 20, 2006 (Article)
DOI: 10.1021/jo052073c

C-Metalated Nitriles: Electrophile-Dependent Alkylations and Acylations

pp 1430–1435
Publication Date (Web): January 24, 2006 (Article)
DOI: 10.1021/jo052102j

Electrolytic Partial Fluorination of Organic Compounds. 83. Anodic Fluorination of N-Substituted Pyrroles and Its Synthetic Applications to gem-Difluorinated Heterocyclic Compounds

pp 1436–1441
Publication Date (Web): January 14, 2006 (Article)
DOI: 10.1021/jo0520745

Synthesis of Highly Substituted Enantiopure Piperazines and Ketopiperazines from Vicinal N-Sulfinyl Diamines

pp 1442–1448
Publication Date (Web): January 14, 2006 (Article)
DOI: 10.1021/jo052077h

Synthesis of New Macrocyclic Chiral Manganese(III) Schiff Bases as Catalysts for Asymmetric Epoxidation

pp 1449–1457
Publication Date (Web): January 25, 2006 (Article)
DOI: 10.1021/jo052113c

Structurally Simple Pyridine N-Oxides as Efficient Organocatalysts for the Enantioselective Allylation of Aromatic Aldehydes

pp 1458–1463
Publication Date (Web): January 14, 2006 (Article)
DOI: 10.1021/jo052132m

Methoxy-Substituted Stilbenes, Styrenes, and 1-Arylpropenes: Photophysical Properties and Photoadditions of Alcohols

pp 1480–1492
Publication Date (Web): January 26, 2006 (Article)
DOI: 10.1021/jo052123d

Syn- and Anti-Selective Prins Cyclizations of δ,ε-Unsaturated Ketones to 1,3-Halohydrins with Lewis Acids

pp 1493–1501
Publication Date (Web): January 25, 2006 (Article)
DOI: 10.1021/jo052142n

The Scope and Limitations of 1,3-Stannyl Shift-Promoted Intramolecular Cyclizations of α-Stannyl Radicals with a Formyl Group

pp 1502–1512
Publication Date (Web): January 12, 2006 (Article)
DOI: 10.1021/jo052176v

Chiral Phosphoramide-Catalyzed Enantioselective Addition of Allylic Trichlorosilanes to Aldehydes. Preparative and Mechanistic Studies with Monodentate Phosphorus-Based Amides

pp 1513–1522
Publication Date (Web): January 17, 2006 (Article)
DOI: 10.1021/jo052202p

Chiral Phosphoramide-Catalyzed Enantioselective Addition of Allylic Trichlorosilanes to Aldehydes. Preparative Studies with Bidentate Phosphorus-Based Amides

pp 1523–1536
Publication Date (Web): January 17, 2006 (Article)
DOI: 10.1021/jo052203h

Boron Trifluoride-Induced, New Stereospecific Rearrangements of Chiral Epoxy Ethers. Ready Access to Enantiopure 4-(Diarylmethyl)-1,3-dioxolanes and 4,5-Disubstituted Tetrahydrobenzo[c]oxepin-4-ols

pp 1537–1544
Publication Date (Web): January 12, 2006 (Article)
DOI: 10.1021/jo052208e

Tether-Directed Selective Synthesis of Fulleropyrrolidine Bisadducts

pp 1545–1551
Publication Date (Web): January 27, 2006 (Article)
DOI: 10.1021/jo052213i

Copper-Promoted Carbon−Nitrogen Bond Formation with 2-Iodo-selenophene and Amides

pp 1552–1557
Publication Date (Web): January 24, 2006 (Article)
DOI: 10.1021/jo052234c

Dimethylzinc-Mediated Alkynylation of Imines

pp 1558–1562
Publication Date (Web): January 20, 2006 (Article)
DOI: 10.1021/jo052273o

Palladium(0)-Catalyzed Synthesis of Chiral Ene-allenes Using Alkenyl Trifluoroborates

pp 1563–1568
Publication Date (Web): January 24, 2006 (Article)
DOI: 10.1021/jo052201x

Metal-Catalyzed Oxidation and Epoxidation of α-Hydroxy Vinyl and Dienyl Sulfoxides

pp 1569–1575
Publication Date (Web): January 21, 2006 (Article)
DOI: 10.1021/jo052244d

Estimating the Limiting Reducing Power of SmI2/H2O/Amine and YbI2/H2O/Amine by Efficient Reduction of Unsaturated Hydrocarbons

pp 1576–1580
Publication Date (Web): January 17, 2006 (Article)
DOI: 10.1021/jo052268k

Scope and Facial Selectivity of the Prins-Pinacol Synthesis of Attached Rings

pp 1581–1587
Publication Date (Web): January 17, 2006 (Article)
DOI: 10.1021/jo0522862

Highly Diastereoselective Enolate Addition of O-Protected α-Hydroxyacetate to (SR)-tert-Butanesulfinylimines: Synthesis of Taxol Side Chain

pp 1588–1591
Publication Date (Web): January 13, 2006 (Article)
DOI: 10.1021/jo052298n

Protonated 2-Methyl-1,2-epoxypropane: A Challenging Problem for Density Functional Theory

pp 1592–1597
Publication Date (Web): January 21, 2006 (Article)
DOI: 10.1021/jo052303n

A Conformationally Flexible, Urea-Based Tripodal Anion Receptor: Solid-State, Solution, and Theoretical Studies

pp 1598–1608
Publication Date (Web): January 21, 2006 (Article)
DOI: 10.1021/jo052339f

Reactions of Cyclohexenyl Iodonium Tetrafluoroborate with Bromide Ion: Retardation Due to the Formation of λ3-Bromoiodane

pp 1609–1613
Publication Date (Web): January 07, 2006 (Article)
DOI: 10.1021/jo0523013

One-Pot Synthesis of Cyclic Nitrones and Their Conversion to Pyrrolizidines: 7a-epi-Crotanecine Inhibits α-Mannosidases

pp 1614–1619
Publication Date (Web): January 27, 2006 (Article)
DOI: 10.1021/jo0523518

Synthesis of Xyloketal A, B, C, D, and G Analogues

pp 1620–1625
Publication Date (Web): January 27, 2006 (Article)
DOI: 10.1021/jo052371+

Diversity-Oriented Synthesis of 3-Iodochromones and Heteroatom Analogues via ICl-Induced Cyclization

pp 1626–1632
Publication Date (Web): January 12, 2006 (Article)
DOI: 10.1021/jo0523722

Synthesis and Reactions of 2,2-[60]Fullerenoalkanoyl Chlorides

pp 1633–1639
Publication Date (Web): January 21, 2006 (Article)
DOI: 10.1021/jo052399l

Synthesis and Characterization of a [3-15N]-Labeled Cis-Syn Thymine Dimer-Containing DNA Duplex

pp 1640–1646
Publication Date (Web): January 13, 2006 (Article)
DOI: 10.1021/jo0524167

Highly Stereoselective β-Anomeric Glycosidation of a 2‘-Deoxy Syn-5‘-Configured 4‘-Spironucleoside

pp 1647–1652
Publication Date (Web): January 31, 2006 (Article)
DOI: 10.1021/jo052324h

Regio- and Stereoselective Synthesis of Aziridino Epoxides from Cyclic Dienes

pp 1653–1657
Publication Date (Web): January 27, 2006 (Article)
DOI: 10.1021/jo052357x

Synthesis and Reactivity of Laquinimod, a Quinoline-3-carboxamide: Intramolecular Transfer of the Enol Proton to a Nitrogen Atom as a Plausible Mechanism for Ketene Formation

pp 1658–1667
Publication Date (Web): January 21, 2006 (Article)
DOI: 10.1021/jo052368q

On the Mechanism of the Skraup−Doebner−Von Miller Quinoline Synthesis

pp 1668–1676
Publication Date (Web): January 24, 2006 (Article)
DOI: 10.1021/jo052410h

Notes

Kinetic Acidity of Supramolecular Imidazolium SaltsEffects of Substituent, Preorientation, and Counterions on H/D Exchange Rates

pp 1688–1691
Publication Date (Web): January 14, 2006 (Note)
DOI: 10.1021/jo052319d

SN2 Reaction of Sulfur Nucleophiles with Hindered Sulfamidates: Enantioselective Synthesis of α-Methylisocysteine

pp 1692–1695
Publication Date (Web): January 13, 2006 (Note)
DOI: 10.1021/jo051632c

Stereoselective Uncatalyzed Synthesis of 2,3-Unsaturated-4-N-substituted-β-O-glycosides by Means of a New d-Galactal-Derived N-(Mesyl)-aziridine

pp 1696–1699
Publication Date (Web): January 19, 2006 (Note)
DOI: 10.1021/jo051877p

Role of Electron Density and Magnetic Couplings on the Nucleus-Independent Chemical Shift (NICS) Profiles of [2.2]Paracyclophane and Related Species

pp 1700–1702
Publication Date (Web): January 17, 2006 (Note)
DOI: 10.1021/jo052095z

Efficient and Green Telescoped Process to 2-Methoxy-3-methyl-[1,4]benzoquinone

pp 1703–1706
Publication Date (Web): January 19, 2006 (Note)
DOI: 10.1021/jo0522512

Symmetrical Bisquinolones via Metal-Catalyzed Cross-Coupling and Homocoupling Reactions

pp 1707–1710
Publication Date (Web): January 12, 2006 (Note)
DOI: 10.1021/jo052283p

Heck, Direct Arylation, and Hydrogenation: Two or Three Sequential Reactions from a Single Catalyst

pp 1711–1714
Publication Date (Web): January 20, 2006 (Note)
DOI: 10.1021/jo0523619

Effective Asymmetric Epoxidation of Styrenes by Chiral Dioxirane

pp 1715–1717
Publication Date (Web): January 24, 2006 (Note)
DOI: 10.1021/jo0520285

First Synthesis of Free Cholesterol−BODIPY Conjugates

pp 1718–1721
Publication Date (Web): January 12, 2006 (Note)
DOI: 10.1021/jo052029x

An Improved Synthesis of Pyran-3,5-dione: Application to the Synthesis of ABT-598, a Potassium Channel Opener, via Hantzsch Reaction

pp 1725–1727
Publication Date (Web): January 20, 2006 (Note)
DOI: 10.1021/jo052226w

Ligand Effects in the Synthesis of N-Heterocycles by Intramolecular Heck Reactions

pp 1732–1735
Publication Date (Web): January 24, 2006 (Note)
DOI: 10.1021/jo0522660

Synthesis of 2-Arylcycloalka-2,4-dienones Using Sulfone-Based Methodology

pp 1736–1738
Publication Date (Web): January 13, 2006 (Note)
DOI: 10.1021/jo0523262

Synthesis of Deuterium-Labeled Derivatives of Dimethylallyl Diphosphate

pp 1739–1741
Publication Date (Web): January 25, 2006 (Note)
DOI: 10.1021/jo052384n

Photochemical Ring Expansion of 4-Azidouracil: a Route to 5H-1,3,5-Triazepin-2,4-dione in the Nucleoside Series

pp 1742–1745
Publication Date (Web): January 21, 2006 (Note)
DOI: 10.1021/jo0524066

Regioselective 6-Endo Cyclizations of 2-Indolylacyl Radicals: Total Synthesis of the Pyrido[4,3-b]carbazole Alkaloid Guatambuine

pp 1746–1749
Publication Date (Web): January 12, 2006 (Note)
DOI: 10.1021/jo052428s

Synthesis of Hydantoins from Enantiomerically Pure α-Amino Amides without Epimerization

pp 1750–1753
Publication Date (Web): January 27, 2006 (Note)
DOI: 10.1021/jo052474s

Additions and Corrections

Substituted 2-Azabicyclo[2.1.1]hexanes as Constrained Proline Analogues: Implications for Collagen Stability.

p 1754
Publication Date (Web): January 20, 2006 (Addition/Correction)
DOI: 10.1021/jo052444p

MTPA (Mosher) Amides of Cyclic Secondary Amines: Conformational Aspects and a Useful Method for Assignment of Amine Configuration.

p 1754
Publication Date (Web): January 26, 2006 (Addition/Correction)
DOI: 10.1021/jo063306i

Can the Absence of Solvation of Neutral Reagents by Ionic Liquids Be Responsible for the High Reactivity in Base-Assisted Intramolecular Nucleophilic Substitutions in These Solvents?

p 1754
Publication Date (Web): January 27, 2006 (Addition/Correction)
DOI: 10.1021/jo063307a
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