Stereodivergent Baylis-Hillman Reaction of a Chiral Acryloyl Imide Exploiting Ion-Chelation Effect: Mechanistic Insight on the Rearrangement of Trichloroacetimidates of the Baylis-Hillman Adducts to Trichloroacetamides |
| |
Authors: | Eleonora Marcucci Gianluca Martelli Mario Orena Samuele Rinaldi |
| |
Affiliation: | (1) Dipartimento di Scienze dei Materiali e della Terra, Università Politecnica delle Marche, Via Brecce Bianche, Ancona, Italy |
| |
Abstract: | Summary. In the presence of DABCO, ethyl glyoxalate and (4S,5R)-1,5-dimethyl-3-acryloyl-4-phenylimidazolidin-2-one gave mixtures of the corresponding Baylis-Hillman adducts enriched in either isomer, depending on the absence or the presence of LiClO4 in the reaction mixture. A diastereomeric mixture in 10:90 dr allowed to definitively establish the mechanism of the reaction leading to trichloroacetamides starting from trichloroacetimidates of the Baylis-Hillman adducts. |
| |
Keywords: | . Stereoselection Chiral imide Chelation Baylis-Hillman Rearrangement. |
本文献已被 SpringerLink 等数据库收录! |