Publication

Enantioselective Synthesis of Quaternary α-Amino Acids Enabled by the Versatility of the Phenylselenonyl Group

Qian Wang, Jieping Zhu, Antonin François Roland Clemenceau
2016
Journal Articles

Abstract

A novel Cinchona alkaloid-catalyzed enantioselective conjugate addition of alpha-alkyl substituted alpha-nitroacetates to phenyl vinyl selenone was developed. The resulting enantio-enriched alpha,alpha-dialkyl substituted alpha-nitroacetates were subsequently converted to various cyclic and acyclic quaternary alpha-amino acids, taking advantage of the rich functionalities of the resulting Michael adducts. Novel protocols allowing chemoselective reduction of phenyl selenone to phenyl selenide and reduction of alkyl phenyl selenones to alkanes are also reported.

Official source

https://infoscience.epfl.ch/entities/publication/9804f356-ee79-4cbf-b90c-d33d67859486

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Qian Wang, Jieping Zhu, Antonin François Roland Clemenceau
2016
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/9804f356-ee79-4cbf-b90c-d33d67859486

About this result

Related concepts (8)

Michael addition reaction

In organic chemistry, the Michael reaction or Michael 1,4 addition is a reaction between a Michael donor (an enolate or other nucleophile) and a Michael acceptor (usually an α,β-unsaturated carbonyl) to produce a Michael adduct by creating a carbon-carbon bond at the acceptor's β-carbon. It belongs to the larger class of conjugate additions and is widely used for the mild formation of carbon-carbon bonds.

Aldol reaction

The aldol reaction (aldol addition) is a reaction that combines two carbonyl compounds (aldehydes or ketones) to form a new β-hydroxy carbonyl compound. These products are known as aldols, from the aldehyde + alcohol, a structural motif seen in many of the products. The use of aldehyde in the name comes from its discovery history, where aldehydes were first used in the reaction and not ketones. Aldol structural units are found in many important molecules, whether naturally occurring or synthetic.

Enantioselective synthesis

Enantioselective synthesis, also called asymmetric synthesis, is a form of chemical synthesis. It is defined by IUPAC as "a chemical reaction (or reaction sequence) in which one or more new elements of chirality are formed in a substrate molecule and which produces the stereoisomeric (enantiomeric or diastereomeric) products in unequal amounts." Put more simply: it is the synthesis of a compound by a method that favors the formation of a specific enantiomer or diastereomer.

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