Skip to content
DraconiticResearch
Search Sources API
182,549 studies31 sourcesUpdated 25 min ago
Peer-reviewedCC BYThe Journal of organic chemistry

Diastereodivergent Morita-Baylis-Hillman Reaction of α,β-Unsaturated N-tert-Butanesulfinyl Imines and Trifluoromethyl Ketones.

  • Ana Sirvent1,2
  • Ester Blanco-López1,2
  • Carmen Nájera2
  • Miguel Yus2
  • Francisco Foubelo1,2
  • José M Sansano1,2
  • María de Gracia Retamosa1,2
  1. 1Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, Alicante03080, Spain.
  2. 2Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, Apdo. 99, Alicante03080, Spain.
Read full textPDFDOICite

Abstract

Herein, we report a stereoselective Morita-Baylis-Hillman protocol to access allylic γ-imino α-trifluoromethyl alcohol adducts. The reaction proceeds under mild and tunable conditions, enabling diastereodivergent access to the two possible stereoisomers through modulation of the Lewis base and additives. The synthetic interest of the resulting compounds as precursors of medicinally relevant fluorinated scaffolds has been demonstrated. A proposal for the reaction mechanism and the stereochemical induction has also been made.

Related

  1. Mechanochemically Accelerated Defluorosilylation of α-Trifluoromethyl Styrenes
    Seishu Ochiai, Daiki Harano, Zhengyu Zhao +1
    ChemRxivPreprintCC BY-NCFull textPharmacology & toxicologyChemRxiv
  2. One-step synthesis of α-fluoroarylacetic acids from trifluoromethyl arenes via photocatalytic reduction
    Huilong Kuang, Suguru Murakami, Tatsushi Yabuta +3
    ChemRxivPreprintCC BY-NC-NDFull textPharmacology & toxicologyChemRxiv
  3. 2‐Chloro‐5‐(trifluoromethyl)aniline‐Derived Schiff Base Palladium(II) Complexes: From Molecular Design to Acute Toxicity Assessment
    Andreea Elena Ştefan, Cristina Elena Dinu‐Pîrvu, Sergiu Shova +8
    ChemistryOpenPeer-reviewedCC BY 4.0Full textOncologyCrossref
  4. Fetal bovine and calf serums differ in their contents of endocannabinoids, unsaturated fatty acids, monoacyl-glycerols, N-acyl-ethanolamines, oxylipins, and cytokines
    Hilal Kalkan, Jean-Philippe C. Lavoie, Isabelle Bourdeau-Julien +3
    Frontiers in ImmunologyPeer-reviewedCC BY 4.0Full textPharmacology & toxicologyCrossrefEurope PMCPMC
  5. Unsaturated fatty acids as immunometabolic modulators in high-risk pregnancies: mechanisms, clinical evidence, and translational perspectives.
    Edmarcio Olinto da Fonseca, Jocilda Carvalho de Faria, Regiane Penaforte Santos +2
    Frontiers in pharmacologyPeer-reviewedCC BYFull textPharmacology & toxicologyEurope PMCCrossref

Cite

BibTeXRIS
BibTeX
@article{sirvent2026diastereodivergent,
  title = {{Diastereodivergent Morita-Baylis-Hillman Reaction of α,β-Unsaturated N-tert-Butanesulfinyl Imines and Trifluoromethyl Ketones.}},
  author = {Ana Sirvent and Ester Blanco-López and Carmen Nájera and Miguel Yus and Francisco Foubelo and José M Sansano and María de Gracia Retamosa},
  journal = {The Journal of organic chemistry},
  year = {2026},
  month = sep,
  doi = {10.1021/acs.joc.6c02039},
  url = {https://europepmc.org/article/MED/42917426},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - Diastereodivergent Morita-Baylis-Hillman Reaction of α,β-Unsaturated N-tert-Butanesulfinyl Imines and Trifluoromethyl Ketones.
AU  - Ana Sirvent
AU  - Ester Blanco-López
AU  - Carmen Nájera
AU  - Miguel Yus
AU  - Francisco Foubelo
AU  - José M Sansano
AU  - María de Gracia Retamosa
PY  - 2026
DA  - 2026/09/01
JO  - The Journal of organic chemistry
DO  - 10.1021/acs.joc.6c02039
UR  - https://europepmc.org/article/MED/42917426
AB  - Herein, we report a stereoselective Morita-Baylis-Hillman protocol to access allylic γ-imino α-trifluoromethyl alcohol adducts. The reaction proceeds under mild and tunable conditions, enabling diastereodivergent access to the two possible stereoisomers through modulation of the Lewis base and additives. The synthetic interest of the resulting compounds as precursors of medicinally relevant fluorinated scaffolds has been demonstrated. A proposal for the reaction mechanism and the stereochemical induction has also been made.
SN  - 0022-3263
SN  - 1520-6904
ER  -