Topics in Current Chemistry Also Available Electronically Topics in Current Chemistry is included in Springer's eBook package Chemistry and Materials Science.If a library does not opt for the whole package the book series ught on a subscription basis. Also,all back volumes are available al For all customers who have a standing order to the print version of Topics in Current Chemistry,we offer the electronic version via SpringerLink free of charge. If you do not have access,you can still view the table of contents of each volume and the abstract of each article by going to the SpringerLink homepage,clicking on "Chemistry and Materials Science,"under Subject Collection,then "Book Series,"under Content Type and finally by selecting Topics in Current Chemistry. You will find information about the cope Instructions for Authors -Sample Contribution at springer.com using the search function by typing in Topics in Current Chemistry. Color figures are published in full color in the electronic version on SpringerLink. Aims and Scope The series Topics in Current Chemistry presents critical reviews of the present and future trends in modem chemical research.The scope includes all areas of chemical science,including the interfaces with related disciplines such as biology,medicine, and materials science. The objective of each thematic volume is to give the non-specialist reader.whether at the un sity or in i ensive overvie of an area where new insights of interest to a larger scientific audience are emerging
Topics in Current Chemistry Also Available Electronically Topics in Current Chemistry is included in Springer’s eBook package Chemistry and Materials Science. If a library does not opt for the whole package the book series may be bought on a subscription basis. Also, all back volumes are available electronically. For all customers who have a standing order to the print version of Topics in Current Chemistry, we offer the electronic version via SpringerLink free of charge. If you do not have access, you can still view the table of contents of each volume and the abstract of each article by going to the SpringerLink homepage, clicking on “Chemistry and Materials Science,” under Subject Collection, then “Book Series,” under Content Type and finally by selecting Topics in Current Chemistry. You will find information about the – Editorial Board – Aims and Scope – Instructions for Authors – Sample Contribution at springer.com using the search function by typing in Topics in Current Chemistry. Color figures are published in full color in the electronic version on SpringerLink. Aims and Scope The series Topics in Current Chemistry presents critical reviews of the present and future trends in modern chemical research. The scope includes all areas of chemical science, including the interfaces with related disciplines such as biology, medicine, and materials science. The objective of each thematic volume is to give the non-specialist reader, whether at the university or in industry, a comprehensive overview of an area where new insights of interest to a larger scientific audience are emerging. vii
Topics in Current Chemistry Also Available Electronically Thus each review within the volume critically surveys one aspect of that topic and places it within the context of the volume as a whole.The most significant developments of the last 5-10 years are presented,using selected examples to illus trate the principles discussed.A description of the laboratory procedures involved is often useful to the reader.The coverage is not exhaustive in data,but rather conceptual,concentrating on the methodological thinking that will allow the non- specialist reader to understand the information presented. Discussion of p ossible futur rch directions in the area is welco ama之 Review articles for the vited b n reference cited as a joumal Impact Factor 2009:4.291:Section"Chemistry,Multidisciplinary":Rank 20of 138
Thus each review within the volume critically surveys one aspect of that topic and places it within the context of the volume as a whole. The most significant developments of the last 5–10 years are presented, using selected examples to illustrate the principles discussed. A description of the laboratory procedures involved is often useful to the reader. The coverage is not exhaustive in data, but rather conceptual, concentrating on the methodological thinking that will allow the nonspecialist reader to understand the information presented. Discussion of possible future research directions in the area is welcome. Review articles for the individual volumes are invited by the volume editors. In references Topics in Current Chemistry is abbreviated Top Curr Chem and is cited as a journal. Impact Factor 2009: 4.291; Section “Chemistry, Multidisciplinary”: Rank 20 of 138 viii Topics in Current Chemistry Also Available Electronically
Preface sts are well aware that it is urgent to develop sustainable processes and to chemical en s that e the effic env onmenta nt cla natural compound ormations into a variety of industrial products based on their multifunctionality and stereochemical diversity.Chemistry using carbohydrates,unprotected or functionalized,continues to be a challenging field of investigation.Because of the complexity of sugars,the issues of regio-and stereoselectivity are among the most difficult to monitor.The low solubility of carbohydrates in several solvents is often a handicap,but some times an op tunity.In this volume,entitled "Carbohydrates and Sustainable t,Part 2-A Mine for Funct and Materials,” vera aspects of the che of ca en pro ses in their conversion into ind ustrial products for cosmetics are ill ustrated b ward transformations using clean solvents and nontoxic catalysis.Othe r contribu tions focus on multistep sequences toward elaborated products,starting from these inexpensive and readily available materials.A survey on the state of the art of ionic liquids derived from sugars is also presented.Synthetic polymers can now be made based on carbohydrate building blocks.The potential of these biocompatible and biodegradable macromolecular materials to replace the polluting petrol um-based rs is also discussed Biod version ard rather c olecules of cal relev an e ha made a akth In all cha pters. and polysacchandes are indeedmine for functional moleculesn This volume,together with the first volume entitled"Carbohydrates and Sus. tainable Development,Part 1-Renewable Resources for Chemistry and Biotech- nology,"demonstrates that a variety of industrial products can be accessed using renewable and low-cost biomass.Both volumes are based on selected papers presented at"Carbohydrates as Organic Raw Materials V-Building a Sustainable Future"(CORM V),held in Lisbon in January 2009.The conferer as chaired by Amelia Pilar Rauter (University of Lisboa and Yves Ou ene au (Unive sity of Lyon.INSA Lyon),in collaboration with Frieder W.Lichtenthaler (Technische ix
Preface Chemists are well aware that it is urgent to develop sustainable processes and to design new chemical entities that improve the efficiency and the environmental impact of chemical transformations. Carbohydrates are the most abundant class of natural compounds: they offer unique structures for multiple transformations into a variety of industrial products based on their multifunctionality and stereochemical diversity. Chemistry using carbohydrates, unprotected or functionalized, continues to be a challenging field of investigation. Because of the complexity of sugars, the issues of regio- and stereoselectivity are among the most difficult to monitor. The low solubility of carbohydrates in several solvents is often a handicap, but sometimes an opportunity. In this volume, entitled “Carbohydrates and Sustainable Development, Part 2 – A Mine for Functional Molecules and Materials,” several aspects of the chemistry of carbohydrates are discussed. Green processes involving their conversion into industrial products for cosmetics are illustrated by straightforward transformations using clean solvents and nontoxic catalysis. Other contributions focus on multistep sequences toward elaborated products, starting from these inexpensive and readily available materials. A survey on the state of the art of ionic liquids derived from sugars is also presented. Synthetic polymers can now be made based on carbohydrate building blocks. The potential of these biocompatible and biodegradable macromolecular materials to replace the polluting petroleum-based polymers is also discussed. Bioconversions toward rather complex molecules of biological relevance have made a breakthrough. In all chapters, evidence is given that sugars and polysaccharides are indeed “a mine for functional molecules and materials.” This volume, together with the first volume entitled “Carbohydrates and Sustainable Development, Part 1 – Renewable Resources for Chemistry and Biotechnology,” demonstrates that a variety of industrial products can be accessed using renewable and low-cost biomass. Both volumes are based on selected papers presented at “Carbohydrates as Organic Raw Materials V – Building a Sustainable Future” (CORM V), held in Lisbon in January 2009. The conference was chaired by Ame´lia Pilar Rauter (University of Lisboa) and Yves Queneau (University of Lyon, INSA Lyon), in collaboration with Frieder W. Lichtenthaler (Technische ix
Preface Universitit Darmstadt)as Honorary Chairman.The CORM meetings were started by Lichtenthaler in 1990.Both volumes highlight the importance of carbohydrates for sustainable processes as abundant,renewable,and low-cost materials and show how sugars contribute significantly to the indispensable new processes for tomorrow's chemistry.With the chemical and biochemical transformations of readily available carbohydrates,we are on the way toward a more sustainable future. Lisbon and Lyon,July 2010 Amelia P.Rauter,University of Lisbor Yves Queneau,University of Lyon
Universita¨t Darmstadt) as Honorary Chairman. The CORM meetings were started by Lichtenthaler in 1990. Both volumes highlight the importance of carbohydrates for sustainable processes as abundant, renewable, and low-cost materials and show how sugars contribute significantly to the indispensable new processes for tomorrow’s chemistry. With the chemical and biochemical transformations of readily available carbohydrates, we are on the way toward a more sustainable future. Lisbon and Lyon, July 2010 Ame´lia P. Rauter, University of Lisbon Yves Queneau, University of Lyon x Preface
Contents Knoevenagel Reaction of Unprotected Sugars. Marie-Christine Scherrmann Carbohydrate-Based Lactones:Synthesis and Applications19 Nuno M. Kavier.Amelia P.Rauter,and Yves Queneau Heterogeneously-Catalyzed Conversion of Carbohydrates................63 Karine De Oliveira Vigier and Frangois Jerome Palladium-Catalyzed Telomerization of Butadiene with Polyols: From Mono to Polysaccharides... .93 Sandrine Bouquillon.Jacques Muzart,Catherine Pinel,and Franck Rataboul Enzymatic Processing of Bioactive Glycosides from Natural Sources...121 Lenka Weignerova and Vladimir Kren Synthetic Poly s from Readily Available Monosaccharides 147 J.A.Galbis and M.G.Garcia-Martin Synthesis and Applications of Ionic Liquids Derived from N tural Suga 177 Cinzia Chiappe,Alberto Marra,and Andrea Mele Index 197 xi
Contents Knoevenagel Reaction of Unprotected Sugars ............................... 1 Marie-Christine Scherrmann Carbohydrate-Based Lactones: Synthesis and Applications . . . . . . . . . . . . . . . 19 Nuno M. Xavier, Ame´lia P. Rauter, and Yves Queneau Heterogeneously-Catalyzed Conversion of Carbohydrates . . . . . . . . . . . . . . . . 63 Karine De Oliveira Vigier and Franc¸ois Je´roˆme Palladium-Catalyzed Telomerization of Butadiene with Polyols: From Mono to Polysaccharides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 93 Sandrine Bouquillon, Jacques Muzart, Catherine Pinel, and Franck Rataboul Enzymatic Processing of Bioactive Glycosides from Natural Sources . . . 121 Lenka Weignerova´ and Vladimı´r Krˇen Synthetic Polymers from Readily Available Monosaccharides . . . . . . . . . . . 147 J.A. Galbis and M.G. Garcı´a-Martı´n Synthesis and Applications of Ionic Liquids Derived from Natural Sugars . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 177 Cinzia Chiappe, Alberto Marra, and Andrea Mele Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 197 xi