164925-87-5Relevant academic research and scientific papers
Copper-Catalyzed Enantioselective Conjugate Addition to α,β-Unsaturated Aldehydes with Various Organometallic Reagents
Goncalves-Contal, Sylvie,Gremaud, Ludovic,Palais, La?titia,Babel, Lucille,Alexakis, Alexandre
, p. 3301 - 3308 (2016)
β-Substituted aldehydes constitute a very important class of compounds found in nature. Synthesis of this motif can be envisioned by C-C bond formation on enals. For this purpose, we report herein the development of enantioselective copper-catalyzed conjugate addition of various organometallic reagents to α,β-unsaturated aldehydes with (R)-H8BINAP, (R)-TolBINAP, and (R)-SEGPHOS as chiral ligands. Three sets of conditions were successfully developed and several enals were used. Reactivity and regio- and enantioselectivities were strongly dependent on reaction conditions and substrates. Good to excellent regio- and enantioselectivities were obtained with zinc reagents R2Zn and aluminum reagents R3Al. However, the asymmetric conjugate addition of Grignard reagents afforded only moderate to good regio- and enantioselectivities.
FRAGRANCE AND FLAVOR MATERIALS
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Page/Page column 34; 46, (2019/12/28)
The synthesis and application of compounds having unique and desired flavor and/or fragrance characteristics are provided herein. The compounds herein can be employed alone or incorporated as fragrance or flavor ingredients in fragrance or flavor compositions. The application is also directed to consumer products comprising such derivatives and/or fragrance or flavor compositions.
Copper-catalyzed asymmetric conjugate addition to challenging michael acceptors and synthesis of relevant target molecules
Gremaud, Ludovic,Palais, Laetitia,Alexakis, Alexandre
scheme or table, p. 196 - 200 (2012/07/28)
We report herein the enantioselective Cu-catalyzed conjugate addition of organometallic reagents to sensitive Michael acceptors and their application to the synthesis of relevant target molecules. This is one of the most important methodologies to form a C-C bond in an enantioselective manner. A wide range of α,β-unsaturated aldehydes and β,γ-unsaturated-α- ketoesters has been successfully used. Reactivity, regioand enantioselectivities were strongly dependent on the reaction conditions, therefore moderate to very good results were obtained. Furthermore, γ-substituted-α-ketoesters were used as chiral building blocks for further derivatization with complete retention of the chiral information to obtain key compounds. Schweizerische Chemische Gesellschaft.
