Development of an α′-hydroxy enone for the aminocatalytic asymmetric formal conjugate addition of aldehydes to acrylates, vinyl ketones and acrolein
- 24 May 2023
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 21 (23) , 4833-4845
Abstract
Formally, a unified enantioselective conjugate addition of aldehydes to acrolein, alkyl–vinyl ketones and acrylic esters is feasible using simple commercially available aminocatalysts and α′-hydroxy enones as self-activated acceptor templates.Keywords
Funding Information
- Gobierno de Navarra (34E/2020)
- Eusko Jaurlaritza (IT1583-22)
- Ministerio de Ciencia e Innovación (PID2019-109633GB/AEI/10.13039/501100011033)
This publication has 84 references indexed in Scilit:
- Combined α,α-dialkylprolinol ether/Brønsted acid promotes Mannich reactions of aldehydes with unactivated imines. An entry to anti-configured propargylic amino alcoholsChemical Science, 2012
- Quantum Mechanical Investigations of Organocatalysis: Mechanisms, Reactivities, and SelectivitiesChemical Reviews, 2011
- Catalytic asymmetric α-alkylation of aldehydesvia a S N 2′-type addition-elimination pathwayChemical Science, 2010
- Enantioselective Organocatalytic Michael Addition of Aldehydes to Trifluoroethylidene MalonatesOrganic Letters, 2010
- Michael Additions to Activated VinylphosphonatesSynthesis, 2009
- First Enantioselective Organocatalytic Conjugate Addition of Aldehydes to Vinyl PhosphonatesOrganic Letters, 2007
- Asymmetric Organocatalytic Domino ReactionsAngewandte Chemie International Edition, 2007
- Synthesis of a Highly Functionalised Azepine via a New TBSOTf-Mediated Cyclisation of a Terminal FormamideSynlett, 2007
- A Novel Heterocycle-Stabilized Allylic Anion Route to Cyclopropanes, 1-Ethoxy-1-vinylethylene Oxides, 1-Hydroxyalkyl 2-Methoxyethyl Ketones, 1-Hydroxyalkyl Vinyl Ketones, .beta.-Ethoxy-.beta.-vinylalkyl Alcohols, .gamma.-Lactones, and .beta.,.gamma.-Unsaturated Carboxylic AcidsThe Journal of Organic Chemistry, 1995
- Asymmetric Diels-Alder reaction: design of chiral dienophilesThe Journal of Organic Chemistry, 1983