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Among several examined Lewis acid catalysts, homogeneous tin chloride catalysts exhibited the best performance to form carbon\u2013carbon bonds. The scope and limitations of the synthesis of five\u2010membered lactones using aldehyde compounds are investigated. The cascade reaction led to high product selectivity as well as diastereoselectivity, and the mechanism leading to the diastereoselectivity was discussed based on isomerization experiments and density functional theory (DFT) calculations. The present results are expected to support new approaches for the efficient utilization of biomass\u2010derived sugars.<\/jats:p>","DOI":"10.1002\/asia.201600307","type":"journal-article","created":{"date-parts":[[2016,4,10]],"date-time":"2016-04-10T12:03:35Z","timestamp":1460289815000},"page":"1731-1737","source":"Crossref","is-referenced-by-count":8,"title":["Cascade Synthesis of Five\u2010Membered Lactones using Biomass\u2010Derived Sugars as Carbon Nucleophiles"],"prefix":"10.1002","volume":"11","author":[{"given":"Sho","family":"Yamaguchi","sequence":"first","affiliation":[{"name":"Department of Environmental Chemistry and Engineering Interdisciplinary Graduate School of Science and Engineering Tokyo Institute of Technology  4259-G1-14 Nagatsuta-cho, Midori-ku Yokohama Kanagawa 226-8502 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Takeaki","family":"Matsuo","sequence":"additional","affiliation":[{"name":"Department of Environmental Chemistry and Engineering Interdisciplinary Graduate School of Science and Engineering Tokyo Institute of Technology  4259-G1-14 Nagatsuta-cho, Midori-ku Yokohama Kanagawa 226-8502 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ken","family":"Motokura","sequence":"additional","affiliation":[{"name":"Department of Environmental Chemistry and Engineering Interdisciplinary Graduate School of Science and Engineering Tokyo Institute of Technology  4259-G1-14 Nagatsuta-cho, Midori-ku Yokohama Kanagawa 226-8502 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Akimitsu","family":"Miyaji","sequence":"additional","affiliation":[{"name":"Department of Environmental Chemistry and Engineering Interdisciplinary Graduate School of Science and Engineering Tokyo Institute of Technology  4259-G1-14 Nagatsuta-cho, Midori-ku Yokohama Kanagawa 226-8502 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Toshihide","family":"Baba","sequence":"additional","affiliation":[{"name":"Department of Environmental Chemistry and Engineering Interdisciplinary Graduate School of Science and Engineering Tokyo Institute of Technology  4259-G1-14 Nagatsuta-cho, Midori-ku Yokohama Kanagawa 226-8502 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2016,5,9]]},"reference":[{"key":"e_1_2_6_1_1","unstructured":"Reviews on Biomass:"},{"volume-title":"Biore-fineries-Industrial Processes and Products, Vol.\u20051: Status Quo and Future Directions","year":"2006","author":"Kamm B.","key":"e_1_2_6_2_2"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr068360d"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr050989d"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/b922014c"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200903028"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.biombioe.2014.11.007"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.201501405"},{"key":"e_1_2_6_9_1","unstructured":"Utilization of carbohydrates:"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja062468t"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja808537j"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1183990"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/cs2000544"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2gc16202d"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11426-014-5283-8"},{"key":"e_1_2_6_16_2","doi-asserted-by":"crossref","unstructured":"M. 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