ArticleChemical science2021
Enantioselective Michael addition to vinyl phosphonates
Article in Chemical science, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 35 citations in OpenAlex.
- Asymmetric Mannich reaction of aromatic imines with malonates in the presence of multifunctional catalysts.Beilstein journal of organic chemistry · 2026Article
- Highly Enantioselective Organocatalysis with Bidentate Halogen Bond Donors.Angewandte Chemie (International ed. in English) · 2025Article
- Enantioselective isothiourea-catalysed reversible Michael addition of aryl esters to 2-benzylidene malononitriles.Chemical science · 2023Article
- Article
- Pushing the limits of the hydrogen bond enhanced halogen bond-the case of the C-H hydrogen bond.Chemical science · 2022Article
- Stereoselective Processes Based on σ-Hole Interactions.Molecules (Basel, Switzerland) · 2022Review
- N-Heterocyclic Iod(az)olium Salts - Potent Halogen-Bond Donors in Organocatalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
Corrections and comments
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Authors and funding
6 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
An asymmetric Michael addition of malononitrile to vinyl phosphonates was accomplished by hydrogen bond-enhanced bifunctional halogen bond (XB) catalysis. NMR titration experiments were used to demonstrate that halogen bonding, with the support of hydrogen-bonding, played a key role in the activation of the Michael acceptors through the phosphonate group. This is the first example of the use of XBs for the activation of organophosphorus compounds in synthesis. In addition, the iodo-perfluorophenyl group proved to be a better directing unit than different iodo- and nitro-substituted phenyl groups. The developed approach afforded products with up to excellent yields and diastereoselectivities and up to good enantioselectivities.
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.