Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, Volume 59 (Chemistry of Heterocyclic Compounds)

Focusing primarily on the literature that has appeared since 1984, Padwa (chemistry, Emory U.) and Pearson (chemistry, U. of Michigan) present 12 contributions that survey applications of [3+2]-cycloadditions in organic synthesis. The chapters cover nitrones, nitronates, azomethine ylides, carbonyl ylides, thiocarbonyl ylides, nitrile oxides, nitrile ylides and nitrile imines, diazoalkanes, azides, mesoionic ring systems, effect of external reagents, and asymmetric reactions

a Comprehensive Reference On The Synthetic Chemistry Of Cycloaddition Reactions

dipolar Cycloaddition Reactions Have Found Many Useful Applications In Chemistry, Particularly With Respect To The Synthesis Of Compounds With New Chiral Centers. Such Asymmetric Syntheses Have A Growing Importance In The Pharmaceutical And Agricultural Industries With Respect To The Preparation Of Chiral Drugs And Natural Products. This Much-needed Volume Updates The Popular 1984 Edition With Advances Made Over The Last Twenty Years In Cycloaddition Reactions. While The 1984 Volume Focused On Theory, Structure, Reactivities, And Selectivities, The New Volume Is Geared Toward Synthetic Applications. Both Carbonyl Ylides And Nitronates, Important Members Of The 1,3-dipole Family That Were Not Reviewed Previously, Are Now Included. Also, Beyond The Capability Of The 1,3-dipolar Cycloadditon Reaction To Produce Heterocycles, The Ability Of Heteroatom-containing Cycloadducts To Transform Into A Variety Of Other Functionalized Organic Molecules, Cylclic Or Acyclic, And The Ability Of Many 1,3-dipolar Cycloadditions To Generate Rings Containing Several Contiguous Stereocenters In One Synthetic Operation Is Discussed. Volume 59 Provides The Only Comprehensive Reference On The Market Detailing The Synthetic Chemistry Of Cycloaddition Reactions.

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cycloaddition Reactions Involve A Great Number Of Bonds Undergoing Transformation During The Reaction, And Produce Products Considerably More Complex Than The Reactants. Recently They Have Been Found To Be Generally Useful For Five-membered Heterocyclic Ring Synthesis, Because Many 1,3-dipolar Species Are Readily Available And React With A Wide Variety Of Dipolarophiles. Here Chemists Focus On Using Such Reactions In Synthesis, Drawing Primarily Information That Has Appeared In The Literature Since 1984. Because Their Emphasis Is On Applications, They Consider Only A Selected Number Of Dipoles, Though Among Them Are Carbonyl Ylides And Nitronates. They Also Keep Discussions About Theoretical And Kinetic Aspects To A Minimum. Annotation C. Book News, Inc., Portland, Or (booknews.com)

Nitrones -- Jason N. Martin and Raymond C.F. Jones Nitronates -- Scott E. Denmark and Jeromy J. Cottell Azomethine ylides -- L.M. Harwood and R.J. Vickers Carbonyl ylides -- Mark C. McMills and Dennis Wright Thiocarbonyl ylides -- Grzegorz Mloston and Heinz Heimgartner Nitrile oxides -- Volker Jager and Pedro A. Colinas Nitrile ylides and nitrile imines -- John T. Sharp Diazoalkanes -- Gerhard Maas Azides -- Chin-Kang Sha and A.K. Mohanakrishnan Mesoionic ring systems -- Gordon W. Gribble Effect of external reagents -- Shuji Kanemasa Asymmetric reactions -- Kurt Vesterager Gothelf and Karl Anker Jorgensen. Dipolar cycloaddition reactions have found many useful applications in chemistry, particularly with respect to the synthesis of compounds with new chiral centers. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products updates the popular 1984 edition, featuring the advances made over the past twenty years and focusing on synthetic applications.