Practical and Highly Stereoselective Synthesis of Trisubstituted (E)-α,β-Unsaturated Esters

Abstract Trisubstituted ( E )-α,β-unsaturated esters bearing various substituents were synthesized with high geometrical selectivity by using three reactions: an aldol reaction, acetylation of the hydroxy group at the β-position, and an E1cB reaction induced by 1,8-diazabicyclo[5.4.0]undec-7-ene. Th...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2015-11, Vol.47 (21), p.3392-3402
Main Authors: Ozeki, Minoru, Egawa, Honoka, Kuse, Akiko, Takano, Toshiki, Yasuda, Narumi, Mizutani, Hideki, Izumiya, Sumire, Nakashima, Daichi, Arimitsu, Kenji, Miura, Takuya, Kajimoto, Tetsuya, Hosoi, Shinzo, Iwasaki, Hiroki, Kojima, Naoto, Node, Manabu, Yamashita, Masayuki
Format: Article
Language:English
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Summary:Abstract Trisubstituted ( E )-α,β-unsaturated esters bearing various substituents were synthesized with high geometrical selectivity by using three reactions: an aldol reaction, acetylation of the hydroxy group at the β-position, and an E1cB reaction induced by 1,8-diazabicyclo[5.4.0]undec-7-ene. The method does not require separation of the diastereoisomeric mixture of β-hydroxy ester intermediates before the E1cB reaction, and is usable for gram-scale syntheses of trisubstituted ( E )-α,β-unsaturated esters.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0034-1378786