Practical and Highly Stereoselective Synthesis of Trisubstituted (E)-α,β-Unsaturated Esters
Minoru Ozeki*, Honoka Egawa, Akiko Kuse, Toshiki Takano, Narumi Yasuda, Hideki Mizutani, Sumire Izumiya, Daichi Nakashima, Kenji Arimitsu, Takuya Miura, Tetsuya Kajimoto, Shinzo Hosoi, Hiroki Iwasaki, Naoto Kojima, Manabu Node, Masayuki Yamashita
*Department of Pharmaceutical Manufacturing Chemistry, Kyoto
Pharmaceutical University, 1 Shichono-cho, Misasagi, Yamashina-ku, Kyoto
607-8414, Japan, Email: ozekim
mb.kyoto-phu.ac.jp
M. Ozeki, H. Egawa, A. Kuse, T. Takano, N. Yasuda, H. Mizutani, S. Izumiya, D. Nakashima, K. Arimitsu, T. Miura, T. Kajimoto, S. Hosoi, H. Iwasaki, N. Kojima, M. Node, M. Yamashita, Synthesis, 2015, 47, 3392-3402.
DOI: 10.1055/s-0034-1378786
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Abstract
A sequence of three reactions enables the synthesis of trisubstituted (E)-α,β-unsaturated esters: an aldol reaction, acetylation of the hydroxy group at the β-position, and an E1cB reaction induced by DBU. The E1cB reaction works with a diastereoisomeric mixture of β-hydroxy ester intermediates. The whole sequence is usable for gram-scale syntheses of trisubstituted (E)-α,β-unsaturated esters.
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Key Words
stereoselective synthesis, enoates, aldol reactions, acylations, elimination reactions, α,β-unsaturated esters
ID: J66-Y2015
