Enantioselective Michael addition to vinyl phosphonates via hydrogen bond-enhanced halogen bond catalysis.
| Autor: | Kaasik M; Department of Chemistry and Biotechnology, Tallinn University of Technology Akadeemia tee 15 12618 Tallinn Estonia tonis.kanger@taltech.ee., Martõnova J; Department of Chemistry and Biotechnology, Tallinn University of Technology Akadeemia tee 15 12618 Tallinn Estonia tonis.kanger@taltech.ee., Erkman K; Department of Chemistry and Biotechnology, Tallinn University of Technology Akadeemia tee 15 12618 Tallinn Estonia tonis.kanger@taltech.ee., Metsala A; Department of Chemistry and Biotechnology, Tallinn University of Technology Akadeemia tee 15 12618 Tallinn Estonia tonis.kanger@taltech.ee., Järving I; Department of Chemistry and Biotechnology, Tallinn University of Technology Akadeemia tee 15 12618 Tallinn Estonia tonis.kanger@taltech.ee., Kanger T; Department of Chemistry and Biotechnology, Tallinn University of Technology Akadeemia tee 15 12618 Tallinn Estonia tonis.kanger@taltech.ee. |
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| Jazyk: | angličtina |
| Zdroj: | Chemical science [Chem Sci] 2021 Apr 26; Vol. 12 (21), pp. 7561-7568. Date of Electronic Publication: 2021 Apr 26. |
| DOI: | 10.1039/d1sc01029h |
| Abstrakt: | 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. Competing Interests: There are no conflicts to declare. (This journal is © The Royal Society of Chemistry.) |
| Databáze: | MEDLINE |
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