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One-Pot Quinine-Catalyzed Synthesis of α-Chiral γ-Keto Esters: Enantioenriched Precursors of cis -α,γ-Substituted-γ-Butyrolactones
- Source :
- Advanced Synthesis & Catalysis. 358:2845-2848
- Publication Year :
- 2016
- Publisher :
- Wiley, 2016.
-
Abstract
- A highly enantioselective one-pot synthesis of important building blocks, α-chiral γ-keto esters, has been developed by combining a quinine-catalyzed Michael addition of malononitrile to trans-enones followed by magnesium monoperoxyphthalate (MMPP) oxidation. These synthons proved to be useful reagents for a simple access to challenging cis-α,γ-disubstituted γ-butyrolactones in good diastereoselectivity and high enantiocontrol.
- Subjects :
- asymmetric synthesis
butyrolactones
Michael addition
organocatalysis
oxidation
Catalysis
Organic Chemistry
010405 organic chemistry
Synthon
Enantioselective synthesis
General Chemistry
Magnesium monoperoxyphthalate
010402 general chemistry
01 natural sciences
0104 chemical sciences
chemistry.chemical_compound
chemistry
Organocatalysis
Reagent
Michael reaction
Organic chemistry
Malononitrile
Subjects
Details
- ISSN :
- 16154150
- Volume :
- 358
- Database :
- OpenAIRE
- Journal :
- Advanced Synthesis & Catalysis
- Accession number :
- edsair.doi.dedup.....09459df1b3cf8648d6b2460676936ce9