title: Mechanistic Insight into a Sugar-Accelerated Tin-Catalyzed Cascade Synthesis of α-Hydroxy-γ-butyrolactone from Formaldehyde.
abstract: Applications of the formose reaction, which involves the formation of sugars from formaldehyde, have previously been confined to the selective synthesis of unprotected sugars. Herein, it is demonstrated that α-hydroxy-γ-butyrolactone (HBL), which is one of the most important intermediates in pharmaceutical syntheses, can be produced from paraformaldehyde. In the developed reaction system, homogeneous tin chloride exhibits high catalytic activity and the addition of mono- and disaccharides accelerates the formation of HBL. These observations suggest that the formose reaction may serve as a feasible pathway for the synthesis of important chemicals.
authors.affiliation: 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), Fax: (+81) 045-924-5441. syamaguchi@chemenv.titech.ac.jp.
authors.forename: Sho
authors.initials: S
authors.lastname: Yamaguchi
authors.affiliation: 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), Fax: (+81) 045-924-5441.
authors.forename: Takeaki
authors.initials: T
authors.lastname: Matsuo
authors.affiliation: 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), Fax: (+81) 045-924-5441.
authors.forename: Ken
authors.initials: K
authors.lastname: Motokura
authors.affiliation: 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), Fax: (+81) 045-924-5441.
authors.forename: Yasuharu
authors.initials: Y
authors.lastname: Sakamoto
authors.affiliation: 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), Fax: (+81) 045-924-5441.
authors.forename: Akimitsu
authors.initials: A
authors.lastname: Miyaji
authors.affiliation: 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), Fax: (+81) 045-924-5441.
authors.forename: Toshihide
authors.initials: T
authors.lastname: Baba
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D005557:Formaldehyde / Q000737:chemistry*; D005947:Glucose / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D017971:Tin Compounds / Q000737:chemistry*
chemical_list: D002241:Carbohydrates; D017971:Tin Compounds; C000610708:alpha-hydroxy-gamma-butyrolactone; D005557:Formaldehyde; D005947:Glucose; D015107:4-Butyrolactone
keywords: carbohydrates; domino reactions; homogeneous catalysis; lactones; sustainable chemistry