0000000001316246

AUTHOR

Daniel Hammerl

showing 2 related works from this author

Asymmetric synthesis of polycyclic 3-fluoroalkylproline derivatives by intramolecular azomethine ylide cycloaddition

2019

The asymmetric synthesis of polycyclic fluorinated proline derivatives has been accomplished by means of an intramolecular azomethine ylide cycloaddition with fluorinated dipolarophiles. Thus, the reaction of benzaldehydes bearing a trifluoromethyl alkene in ortho position with an azomethine ylide precursor derived from chiral 2-amino indanol takes place with excellent levels of diastereoselectivity, with simultaneous generation of four stereocenters. In order to determine the influence of the fluorine moiety in the process, starting material bearing non-fluorinated alkenes were synthesised. In this case, a dramatic drop of selectivity occurred, which indicates that the role of the fluorine…

chemistry.chemical_classificationTrifluoromethyl010405 organic chemistryAlkeneOrganic ChemistryEnantioselective synthesisSubstituentAzomethine ylide010402 general chemistry01 natural sciencesMedicinal chemistryCycloaddition0104 chemical sciencesStereocenterchemistry.chemical_compoundchemistryIntramolecular force
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CCDC 1899383: Experimental Crystal Structure Determination

2019

Related Article: Fernando Rabasa-Alcañiz, Daniel Hammerl, Anabel Sánchez-Merino, Tomás Tejero, Pedro Merino, Santos Fustero, Carlos del Pozo|2019|Org.Chem.Front.|6|2916|doi:10.1039/C9QO00525K

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters7-(trifluoromethyl)-6a77a1014b15a-hexahydro-6H8H9aH-[1]benzopyrano[3'4':45]pyrrolo[12-d]indeno[21-b][14]oxazin-8-oneExperimental 3D Coordinates
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