Work

Z-Selective Synthesis of Trisubstituted Alkenes by the HWE Reaction Using Modified Still–Gennari Type Reagents

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide Application of new reagents in the Z -selective synthesis of trisubstituted alkenes via modified Horner–Wadsworth–Emmons carbonyl olefination is presented. The reagents tested are ethyl bis(1,1,1,3,3,3-hexafluoroisopropyl)phosphonoalkanoates, structurally similar to Still–Gennari type reagents. A set of various trisubstituted Z -alkenes was obtained in very high or quantitative yields with excellent Z -selectivity. Remarkably, the procedure was very successful for the synthesis of Z -2-aryl-substituted cinnamic acid esters, maintaining exclusive Z -selectivity even at an increased temperature.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.5c00470

Author: Ignacy Janicki

Institutions: Centrum Badań Molekularnych i Makromolekularnych Polskiej Akademii Nauk, Polish Academy of Sciences

Language: English

Topic: Phosphorus compounds and reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funder: Centrum Badań Molekularnych i Makromolekularnych Polskiej Akademii Nauk