Synthesis, Inhaltsverzeichnis PAPER © Georg Thieme Verlag Stuttgart ˙ New York A Convenient Synthesis of the (E)-Monoacetates of 2-Alkylidenepropane-1,3-diols Tsuyoshi Miura, Kenjiro Okazaki, Kyoko Ogawa, Erika Otomo, Satoe Umetsu, Mauko Takahashi, Yuya Kawashima, Yuki Jyo, Naka Koyata, Yasuoki Murakami, Nobuyuki Imai*Faculty of Pharmacy, Chiba Institute of Science, 15-8 Shiomi-cho, Choshi, Chiba 288-0025, JapanFax: +81(479)304610; e-Mail: nimai@cis.ac.jp; Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract Various kinds of 3-substituted (E)-2-(hydroxymethyl)prop-2-enyl acetates were conveniently obtained in excellent yields by the regiospecific acetylation of 2-alkylidenepropane-1,3-diols with 10 equivalents of vinyl acetate in the presence of 50% w/w porcine pancreatic lipase (PPL) type II; the starting materials or (Z)-monoacetate or diacetate byproducts were generally not present. Key words (E)-monoacetates - acetylation - diols - regioselectivity - lipase Volltext Referenzen References 1 Greene TW. Wuts PGM. Protective Groups in Organic Synthesis 3rd ed.: John Wiley and Sons; New York: 1999. 2a Faber K. Biotransformations in Organic Chemistry Springer; Berlin: 2000. 2b Wong C.-H. Whitesides GM. Enzymes in Synthetic Organic Chemistry Pergamon; Oxford: 1994. 3a Hisano T. Onodera K. Toyabe Y. Mase N. Yoda H. Takabe K. Tetrahedron Lett. 2005, 46: 6293 ; and references cited therein 3b Takabe K. Mase N. Hisano T. Yoda H. Tetrahedron Lett. 2003, 44: 3267 4 Miura T. Kawashima Y. Takahashi M. Murakami Y. Imai N. Synth. Commun. 2007, 37: 3105 5 Miura T. Kawashima Y. Umetsu S. Kanamori D. Tsuyama N. Jyo Y. Murakami Y. Imai N. Chem. Lett. 2007, 36: 814 6a Gu J.-X. Holland HL. Synth. Commun. 1998, 28: 3305 6b Hon Y.-S. Lu L. Tetrahedron 1995, 51: 7937 7 Cho J.-H. Ko SY. Oh E. Park JC. Yoo JU. Helv. Chim. Acta 2002, 85: 3994
