Back to results
US 11,434,253 B2Granted
Enantiopure terphenyls with two ortho-atropisomeric axes
AssigneesUniversite De Strasbourg, Centre National De La Recherche Scientifique
InventorsQuentin Dherbassy, Joanna Wencel-Delord, Françoise Colobert, Gaspard Hedouin
Life of this patent
Estimating the term…
Abstract
Enantiopure terphenyl presenting two ortho-located chiral axes having the following structural formula (I): their process of synthesis and their use as mono or bidentate ligands for asymmetric organometallic reactions, as organocatalysts, as chiral base and as generator, with metal, of isolable chiral metallic complexes for applications in asymmetric catalysis and others.
Claims14
Enantiopure terphenyl presenting two ortho-located chiral axis having the following structural formula (I)
- wherein
- R1 on the phenyl ring Ar1 represents
- a halogen atom, or
- a substituted or unsubstituted branched or straight alkyl group, or
- a substituted or unsubstituted cycloalkyl group, or
- a substituted or unsubstituted branched or straight alkoxy group, or
- a CH2F group, or a CHF2 group or a —CnFn+2 group with n=1 to 10 or,
- a substituted or unsubstituted aryl group or,
- a —CORa or a —COORa group with Ra selected from a substituted or unsubstituted branched or straight alkyl group or a substituted or unsubstituted aryl group or
- a —NRbRc group with Rb and Rc independently selected from a hydrogen atom, a substituted or unsubstituted branched or straight alkyl group or a substituted or unsubstituted aryl group or forming a NH2-protecting group, or
- a BRaRb group with Ra and Rb, identical or different being as defined above or
- a —B(ORd)(ORe) group with Rd and Re identical or different being selected from a hydrogen atom or a substituted or unsubstituted branched or straight alkyl group,
- R2 in position 4 or 5 of the phenyl ring Ar1 which bears it represents
- a hydrogen atom or
- a halogen atom,
- a substituted or unsubstituted branched or straight alkyl group or
- a substituted or unsubstituted cycloalkyl group, or
- a substituted or unsubstituted branched or straight alkoxy group or
- a substituted or unsubstituted aryl group or
- a —CORa or a —COORa group with Ra selected from a substituted or unsubstituted branched or straight alkyl group or a substituted or unsubstituted aryl group, or
- a —NRbRc group with Rb and Rc independently selected from a hydrogen atom, a substituted or unsubstituted branched or straight alkyl group, or a substituted or unsubstituted aryl group, or forming a NH2-protecting group or
- a —BRaRb group with Ra and Rb identical or different being as defined above or,
- a —B(ORd)(ORe) group with Rd and Re identical or different being selected from a hydrogen atom or a substituted or unsubstituted branched or straight alkyl group,
- R3 on the phenyl ring Ar1 represents
- a halogen atom or
- a substituted or unsubstituted branched or straight alkyl group or,
- a substituted or unsubstituted cycloalkyl group, or
- a substituted or unsubstituted branched or straight alkoxy group or
- a substituted or unsubstituted aryl group or
- a —CORa or a —COORa group with Ra selected from a substituted or unsubstituted branched or straight alkyl group or a substituted or unsubstituted aryl group, or
- a —NRbRc group with Rb and Rc independently selected from a hydrogen atom, a substituted or unsubstituted branched or straight alkyl group, or a substituted or unsubstituted aryl group, or forming a NH2-protecting group,
- a —BRaRb group with Ra and Rb identical or different being as defined above or,
- a —B(ORd)(ORe) group with Rd and Re identical or different being selected from a hydrogen atom or a substituted or unsubstituted branched or straight alkyl group,
- R4, which may be in position 2, 3, 4 or 5 on the phenyl ring Art which bears it, represents:
- a hydrogen atom or
- a halogen atom or
- a substituted or unsubstituted branched or straight alkyl group or,
- a substituted or unsubstituted cycloalkyl group, or
- a CH2F group, or a CHF2 group or —CnFn+2 group with n=1 to 10, or
- a substituted or unsubstituted aryl group, or
- a —ORa, a —CORa or a —COORa group with Ra selected from a substituted or unsubstituted branched or straight alkyl group or a substituted or unsubstituted aryl group, or
- a —NRbRc group with Rb and Rc independently selected from a hydrogen atom, a substituted or unsubstituted branched or straight alkyl group, or a substituted or unsubstituted aryl group, or forming a NH2-protecting group, or
- a —BRaRb group with Ra and Rb identical or different being as defined above or,
- a —B(ORd)(ORe) group with Rd and Re identical or different being selected from a hydrogen atom or a substituted or unsubstituted branched or straight alkyl group,
- R5 on the phenyl ring Art represents a coordinating group or a substituent that will be used to install a coordinating group, selected from:
- a halogen atom,
- an —ORb group with Rb selected from a hydrogen atom, a substituted or unsubstituted branched or straight alkyl group, or a substituted or unsubstituted aryl group, or a NH2-protecting group or
- a —CH2ORb group with Rb selected from a hydrogen atom, a substituted or unsubstituted branched or straight alkyl group, or a substituted or unsubstituted aryl group, or
- a —CHO group or
- a —COORb group with Rb selected from a hydrogen atom, a substituted or unsubstituted branched or straight alkyl group, or a substituted or unsubstituted aryl group, or a NH2-protecting group, or
- a —NRbRc group with Rb and Rc independently selected from a hydrogen atom, a substituted or unsubstituted branched or straight alkyl group, or a substituted or unsubstituted aryl group, or a NH2-protecting group,
- a —SORa group or a —SRa group or a —SO2Ra with Ra selected from a substituted or unsubstituted branched or straight alkyl group or a substituted or unsubstituted aryl group, or
- a —PRaRd or a —P (O)Rand with Ra and Rd independently selected from a substituted or unsubstituted branched or straight alkyl group or a substituted or unsubstituted aryl group, or
- a —C═NRb with Rb as defined above or
- a substituted or unsubstituted oxazoline group or
- a substituted or unsubstituted indenyl group or
- a substituted or unsubstituted cyclopentadienyl group,
- R6 on the phenyl ring Ar3 is a coordinating group
- either represents
- a hydrogen atom or
- a halogen atom,
- an —OH group
- a substituted or unsubstituted branched or straight alkyl group or
- a substituted or unsubstituted cycloalkyl group, or
- a substituted or unsubstituted aryl group or
- a —SORa group or a —SRa group or a —SO2Ra with Ra selected from a substituted or unsubstituted branched or straight alkyl group or a substituted or unsubstituted aryl group, or
- a —ORa, a —CORa or a —COORa group with Ra selected from a substituted or unsubstituted branched or straight alkyl group or a substituted or unsubstituted aryl group, or
- a —NRbRc group with Rb and Rc independently selected from a hydrogen atom, a substituted or unsubstituted branched or straight alkyl group, or a substituted or unsubstituted aryl group, or forming a NH2-protecting group or,
- a —BRaRb group with Ra and Rb identical or different being as defined above or,
- a —B(ORd)(ORe) group with Rd and Re identical or different being selected from a hydrogen atom or a substituted or unsubstituted branched or straight alkyl group,
- a —PRaRd or a —P (O)RaRd with Ra and Rd independently selected from a substituted or unsubstituted branched or straight alkyl group or a substituted or unsubstituted aryl group, or
- a substituted or unsubstituted or oxazoline group
- a substituted or unsubstituted indenyl group or
- a substituted or unsubstituted cyclopentadienyl group,
- or may form with R5
- a bridged phosphoric acid or ester or phosphinate represented by formula
- with X being a carbon or an oxygen atom and Ra selected from a hydrogen atom or a substituted or unsubstituted branched or straight alkyl group;
- or
- a bridged phosphoramidite or phosphoramine represented by formula
- with X being a carbon or an oxygen atom and Ra and Rb selected from a substituted or unsubstituted branched or straight alkyl group or a substituted or unsubstituted aryl group,
- R7 which may be in position 3 or 4 on the phenyl ring Ar3 which bears it represents:
- a hydrogen atom or
- a halogen atom or
- a substituted or unsubstituted branched or straight alkyl group or,
- a substituted or unsubstituted branched or straight alkoxy group
- a substituted or unsubstituted cycloalkyl group, or
- a CH2F group, or a CHF2 group or —CnFn+2 group with n=1 to 10, or
- a substituted or unsubstituted aryl group, or
- a —ORa, a —CORa or a —COORa group with Ra selected from a substituted or unsubstituted branched or straight alkyl group or a substituted or unsubstituted aryl group, or
- a —NRbRc group with Rb and Rc independently selected from a hydrogen atom, a substituted or unsubstituted branched or straight alkyl group, or a substituted or unsubstituted aryl group, or forming a NH2-protecting group, or
- a —BRaRb group with Ra and Rb identical or different being as defined above or,
- a —B(ORd)(ORe) group with Rd and Re identical or different being selected from a hydrogen atom or a substituted or unsubstituted branched or straight alkyl group, R8 on the phenyl ring Ar3 represents
- a halogen atom or
- a substituted or unsubstituted branched or straight alkyl group, or a substituted or unsubstituted branched or straight alkoxy group or
- a —ORa group with Ra selected from a substituted or unsubstituted branched or straight alkyl group or a substituted or unsubstituted aryl group, or
- a substituted or unsubstituted aryl group or
- a —CORa or a —COORa group with Ra selected from a substituted or unsubstituted branched or straight alkyl group or a substituted or unsubstituted aryl group, or
- a —NRbRc group with Rb and Rc independently selected from a hydrogen atom, a substituted or unsubstituted branched or straight alkyl group, or a substituted or unsubstituted aryl group, or a forming NH2-protecting group, or
- a —BRaRb group with Ra and Rb identical or different being as defined above or,
- a —B(ORd)(ORe) group with Rd and Re identical or different being selected from a hydrogen atom or a substituted or unsubstituted branched or straight alkyl group.
97 more elements
Dependencies are inferred from the claim text.