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Synthesis 2008(17): 2695-2700  
DOI: 10.1055/s-2008-1067211
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, Japan
Fax: +81(479)304610; e-Mail: nimai@cis.ac.jp;
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Publication History

Received 16 April 2008
Publication Date:
06 August 2008 (online)

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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

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