期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 28, 期 5, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202103874
关键词
enantioselectivity; fluorine; kinetic resolution; organocatalysis; polyketide
资金
- Agence Nationale de la Recherche [ANR-19-CE07-0033, ANR-18-CE07-0036]
- Centre National de la Recherche Scientifique (CNRS)
- Aix-Marseille Universite
- China Scholarship Council [201908070004]
- Agence Nationale de la Recherche (ANR) [ANR-19-CE07-0033] Funding Source: Agence Nationale de la Recherche (ANR)
The authors developed a simple strategy to synthesize enantioenriched complex acyclic stereotriads with fluorinated tetrasubstituted stereocenters, by combining a diastereoselective aldol-Tishchenko reaction and an enantioselective organocatalyzed kinetic resolution in two unprecedented steps. The aldol-Tishchenko reaction directly generated a large panel of acyclic 1,3-diols possessing a fluorinated tetrasubstituted stereocenter with excellent diastereocontrol, while the subsequent organocatalyzed kinetic resolution produced the desired enantioenriched stereotriads with high selectivity.
Elaboration of enantioenriched complex acyclic stereotriads represents a challenge for modern synthesis even more when fluorinated tetrasubstituted stereocenters are targeted. We have been able to develop a simple strategy in a sequence of two unprecedented steps combining a diastereoselective aldol-Tishchenko reaction and an enantioselective organocatalyzed kinetic resolution. The aldol-Tish-chenko reaction directly generates a large panel of acyclic 1,3-diols possessing a fluorinated tetrasubstituted stereocenter by condensation of fluorinated ketones with aldehydes under very mild basic conditions. The anti 1,3-diols featuring three contiguous stereogenic centers are generated with excellent diastereocontrol (typically >99:1 dr). Depending upon the precursors both diastereomers of stereotriads are accessible through this flexible reaction. Furthermore, from the obtained racemic scaffolds, development of an organocatalyzed kinetic resolution enabled to generate the desired enantioenriched stereotriads with excellent selectivity (typically er >95:5).
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