Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, Volume 59 PDF
Preview Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, Volume 59
TheChemistryofHeterocyclicCompounds,Volume59:SyntheticApplicationsof1,3-DipolarCycloadditionChemistry TowardHeterocyclesandNaturalProducts.EditedbyAlbertPadwaandWilliamH.Pearson. Copyright#2002JohnWiley&Sons,Inc. ISBN:0-471-38726-6 SYNTHETIC APPLICATIONS OF 1,3-DIPOLAR CYCLOADDITION CHEMISTRY TOWARD HETEROCYCLES AND NATURAL PRODUCTS Thisisthefifty-ninthvolumeintheseries THECHEMISTRYOFHETEROCYCLICCOMPOUNDS THECHEMISTRY OFHETEROCYCLIC COMPOUNDS ASERIESOFMONOGRAPHS EDWARD C.TAYLOR ANDPETERWIPF, Editors ARNOLDWEISSBERGER, FoundingEditor SYNTHETIC APPLICATIONS OF 1,3-DIPOLAR CYCLOADDITION CHEMISTRY TOWARD HETEROCYCLES AND NATURAL PRODUCTS Edited by Albert Padwa DepartmentofChemistry EmoryUniversity William H. Pearson DepartmentofChemistry UniversityofMichigan ANINTERSCIENCE1PUBLICATION JOHNWILEY&SONS,INC. Designationsusedbycompaniestodistinguishtheirproductsareoftenclaimedastrademarks. InallinstanceswhereJohnWiley&Sons,Inc.,isawareofaclaim,theproductnamesappear ininitialcapitalorALLCAPITALLETTERS.Readers,however,shouldcontacttheappropriatecompaniesfor morecompleteinformationregardingtrademarksandregistration. Copyright#2002byJohnWiley&Sons,Inc.,NewYork.Allrightsreserved. Nopartofthispublicationmaybereproduced,storedinaretrievalsystemortransmittedinany formorbyanymeans,electronicormechanical,includinguploading,downloading,printing, decompiling,recordingorotherwise,exceptaspermittedunderSections107or108ofthe1976 UnitedStatesCopyrightAct,withoutthepriorwrittenpermissionofthePublisher.Requeststo thePublisherforpermissionshouldbeaddressedtothePermissionsDepartment,JohnWiley&Sons, Inc.,605ThirdAvenue,NewYork,NY10158-0012,(212)850-6011,fax(212)850-6008, E-Mail:[email protected]. Thispublicationisdesignedtoprovideaccurateandauthoritativeinformationinregardtothe subjectmattercovered.Itissoldwiththeunderstandingthatthepublisherisnotengagedinrendering professionalservices.Ifprofessionaladviceorotherexpertassistanceisrequired,theservicesofa competentprofessionalpersonshouldbesought. ISBN0-471-22190-2 ThistitleisalsoavailableinprintasISBN0-471-38726-6. FormoreinformationaboutWileyproducts,visitourwebsiteatwww.Wiley.com. The Chemistry of Heterocyclic Compounds Introduction to the Series The chemistry of heterocyclic compounds is one of the most complex and intriguing branches of organic chemistry, of equal interest for its theoretical implications,forthediversityofitssyntheticprocedures,andforthephysiological and industrial significance of heterocycles. TheChemistryofHeterocyclicCompoundshasbeenpublishedsince1950under the initial editorship of Arnold Weissberger, and later, until his death in 1984, under the joint editorship of Arnold Weissberger and Edward C. Taylor. In 1997, Peter Wipf joined Prof. Taylor as editor. This series attempts to make the extraordinarily complex and diverse field of heterocyclic chemistry as organized and readily accessible as possible. Each volume has traditionally dealt with syntheses, reactions, properties, structure, physical chemistry, and utility of com- pounds belonging to a specific ring system or class (e.g., pyridines, thiophenes, pyrimidines, three-membered ring systems). This series has become the basic reference collection for information on heterocyclic compounds. Manybroaderaspectsofheterocyclicchemistryarerecognizedasdisciplinesof general significance that impinge on almost all aspects of modern organic chemistry, medicinal chemistry, and biochemistry, and for this reason we initiated several years ago a parallel series entitled General Heterocyclic Chemistry, which treated such topics as nuclear magnetic resonance, mass spectra, and photoche- mistry of heterocyclic compounds, the utility of heterocycles in organic synthesis, and the synthesis of heterocycles by means of 1,3-dipolar cycloaddition reactions. These volumes were intended to be of interest to all organic, medicinal, and biochemically oriented chemists, as well as to those whose particular concern is heterocyclic chemistry. It has, however, become increasingly clear that the above distinction between the two series was unnecessary and somewhat confusing, and we have therefore elected to discontinue General Heterocyclic Chemistry and to publish all forthcoming volumes in this general area in The Chemistry of Hetero- cyclic Compounds series. Itisamajorchallengetokeepourcoverageofthisimmensefielduptodate.One strategyistopublishSupplementsornewPartswhenmeritedbytheamountofnew material, as has been done, inter alia, with pyridines, purines, pyrimidines, quinazolines, isoxazoles, pyridazines and pyrazines. The chemistry and applica- tions to synthesis of 1,3-dipolar cycloaddition reactions in the broad context of organicchemistrywerefirstcoveredinawidelycitedtwo-volumetreatiseeditedby Prof.AlbertPadwathatappearedin1984.Sincesomuchhasbeenpublishedonthis fascinating and broadly useful subject in the intervening years, we felt that a Supplementwouldbewelcomedbytheinternationalchemistrycommunity,andwe vi The Chemistryof Heterocyclic Compounds:Introduction totheSeries are immensely grateful to Prof. Padwa and Prof. Pearson for tackling this arduous task.Theresult isanother outstanding contributiontothe organicand heterocyclic chemistry literature that we are delighted to publish within The Chemistry of Heterocyclic Compounds series. EDWARD C. TAYLOR DepartmentofChemistry PrincetonUniversity Princeton,NewJersey PETERWIPF DepartmentofChemistry UniversityofPittsburgh Pittsburgh,Pennsylvania Preface Cycloaddition reactions figure prominently in both synthetic and mechanistic organic chemistry. The current understanding of the underlying principles in this areahasgrownfromafruitfulinterplaybetweentheoryandexperiment.Themonu- mental work of Rolf Huisgen and co-workers in the early 1960s led to thegeneral conceptof1,3-dipolarcycloaddition.Fewreactionsrivalthisprocessinthenumber of bonds that undergo transformation during the reaction, producing products considerably more complex than the reactants. Over the years, this reaction has developed into a generally useful method for five-membered heterocyclic ring synthesis,sincemany1,3-dipolarspeciesarereadilyavailableandreactwithawide variety of dipolarophiles. The last comprehensive survey of this area dates back to 1984, when the two- volume set edited by Padwa, ‘‘1,3-Dipolar Cycloaddition Chemistry,’’ appeared. Since then, substantial gains in the synthetic aspects of this chemistry have dominated the area, including both methodology development and a body of creative and conceptually new applications of these [3þ2]-cycloadditions in organic synthesis. The focus of this volume centers on the utility of this cycloaddition reaction in synthesis, and deals primarily with information that has appeared in the literature since 1984. Consequently, only a selected number of dipoles are reviewed, with a major emphasis on synthetic applications. Both carbonyl ylides and nitronates, important members of the 1,3-dipole family that were not reviewed previously, are now included. Discussion of the theoretical, mechanistic, and kinetic aspects of the dipolar-cycloaddition reaction have been kept to a minimum, butreferences to important new work in these areas aregiven throughout the 12 chapters. Beyond the ability of the 1,3-dipolar cycloaddition reaction to produce hetero- cycles,itsimportanceextendstotwootherareasoforganicsynthesis,bothofwhich are included in the current volume. First, the heteroatom-containing cycloadducts may be transformed into a variety of other functionalized organic molecules, whethercyclicoracyclic.Second,many1,3-dipolarcycloadditionshavetheability to generate rings (and functionality derived from transformations of such rings) containing several contiguous stereocenters in one synthetic operation. The con- figurations of these new stereocenters arise from the geometry of the dipole and dipolarophile as well as the topography (endo or exo) of the cycloaddition. An additional stereochemical feature arises when the reactive p faces of either of the cycloaddends are diastereotopic. Relative stereocontrol in 1,3-dipolar cycloaddi- tions is dealt with in some detail, and asymmetric versions of these dipolar cycloadditions represent an entirely new aspect of the current reference work. Inrecentyears,numerousnaturalandunnaturalproductshavebeenpreparedby synthetic routes that have a 1,3-dipolar cycloaddition as a crucial step in their viii Preface synthesis. Consequently, this reaction has become recognized as an extremely important transformation in the repertoire of the synthetic organic chemist. ALBERT PADWA DepartmentofChemistry EmoryUniversity Atlanta,Georgia WILLIAM H. PEARSON DepartmentofChemistry UniversityofMichigan AnnArbor,Michigan Contents 1 NITRONES 1 Raymond C. F. Jones 2 NITRONATES 83 Scott E. Denmark and Jeromy J. Cottell 3 AZOMETHINE YLIDES 169 L. M. Harwood and R. J. Vickers 4 CARBONYL YLIDES 253 Mark C. McMills and Dennis Wright 5 THIOCARBONYL YLIDES 315 Grzegorz Mloston and Heinz Heimgartner 6 NITRILE OXIDES 361 Volker Jager and Pedro A. Colinas 7 NITRILE YLIDES AND NITRILE IMINES 473 John T. Sharp 8 DIAZOALKANES 539 Gerhard Maas 9 AZIDES 623 Chin-Kang Sha and A. K. Mohanakrishnan 10 MESOIONIC RING SYSTEMS 681 Gordon W. Gribble 11 EFFECT OF EXTERNAL REAGENTS 755 Shuji Kanemasa 12 ASYMMETRIC REACTIONS 817 Kurt Vesterager Gothelf and Karl Anker Jorgensen INDEX 901 SYNTHETIC APPLICATIONS OF 1,3-DIPOLAR CYCLOADDITION CHEMISTRY TOWARD HETEROCYCLES AND NATURAL PRODUCTS Thisisthefifty-ninthvolumeintheseries THECHEMISTRYOFHETEROCYCLICCOMPOUNDS
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