1428976-33-3Relevant academic research and scientific papers
Origin of the E/Z Selectivity in the Synthesis of Tetrasubstituted Olefins by Wittig Reaction of α-Fluorophosphonium Ylides: An Explanation for the Low Stereoselectivity Observed in Reactions of α-Alkoxy Aldehydes
Depré, Dominique,Vermeulen, Wim A. A.,Lang, Yolande,Dubois, Jean,Vandevivere, Jan,Vandermeersch, Jeremy,Huang, Longchuan,Robiette, Rapha?l
, p. 1414 - 1417 (2017/03/23)
A series of tetrasubstituted fluoroalkenes were synthesized in good yield and high E/Z selectivity (up to 96/4) by Wittig reaction between α-heterosubstituted ketones and α-fluorophosphonium ylides. A detailed study of factors that control stereoselectivity in these reactions shows that stereoselectivity is the result of stabilizing CH···F and N···C=O interactions in the addition TS leading to the E isomer. This analysis provides a rationale for the observed decrease in selectivity for reactions of stabilized ylides with α-alkoxy aldehydes.
IMPROVED PROCESS FOR PREPARING 2-[(2E)-2-FLUORO-2-(3-PIPERIDINYLIDENE)ETHYL]-1H-ISOINDOLE-1,3(2H)-DIONE
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Page/Page column 20, (2013/04/13)
The present invention relates to an improved process for preparing 2-[(2E)-2-fluoro-2-(3-piperidinylidene)ethyl]-1H-isoindole-1,3(2H)-dione, or a salt thereof, which is an intermediate in the synthesis route of the antibacterial compound 7-[(3E)-3-(2-amin
