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Synthesis 2015; 47(21): 3392-3402
DOI: 10.1055/s-0034-1378786
DOI: 10.1055/s-0034-1378786
paper
Practical and Highly Stereoselective Synthesis of Trisubstituted (E)-α,β-Unsaturated Esters
Further Information
Publication History
Received: 15 April 2015
Accepted after revision: 04 June 2015
Publication Date:
24 July 2015 (online)
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.
Key words
stereoselective synthesis - enoates - aldol reactions - acylations - elimination reactionsSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1378786.
- Supporting Information
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