Aminated compounds bearing at least an allyl and a difluoromethyl and method used for synthesis thereof

A compound comprising at least one carbon bearing:

• an amine function;
• an allyl or propargyl radical;
• a difluoromethylene group;
• and
• a hydrogen or a hydrocarbon-based radical which is electron-donating
• or weakly electron-withdrawing with a σp≦0.2

A method for synthesizing a compound of formula I:

• wherein:
• Rf represents a carbon radical bearing a difluoromethylene group providing the link with the rest of the molecule, of at most 15 carbon atoms;
• R1 represents a hydrogen, an alkyl or aralkyl radical;
• R2 represents a hydrogen, an alkyl, aralkyl, or an aryl radical;
• R3 represents a hydrogen, alkyl, including aralkyl, an aryl radical, or forms, with R4, an additional double bond so as to convert the allyl radical into a propargyl radical;
• R4 represents a hydrogen, aryl, alkyl, aralkyl, or, with R3, forms an additional double bond so that the ethylenic bond becomes acetylenic, making it possible to go from an allyl radical to a propargyl radical;
• R5 represents a hydrogen, an aryl, an alkyl, or aralkyl radical;
• R5 and R4 optionally being fractions of said “Ar” group above, such that R5 and R4, and also the carbon which bears them, form a radical Ar;
• optionally, one of R1, R2, R4, R3 and R5 being a specific trivalent, nitrile or acid function, optionally in esterified form;
• R′ is a hydrogen, a protective group, an aryl, an alkyl, or aralkyl, optionally, a chiral alkyl or aralkyl;
• and
• R″ is an allyl radical, a hydrogen, a metal cation, or a fraction of metal cations when the metal is polyvalent;
• said method comprising the step of:
• a) reacting an allyl organometallic on an imine bearing difluoromethylene groups, and
• b) recovering the product obtained in step a).

A process for cyclizing metathesis, comprising the step of using as substrate a compounds of formula (I):

• wherein:
• wherein:
• Rf represents a carbon radical bearing a difluoromethylene group providing the link with the rest of the molecule, of at most 15 carbon atoms;
• R1 represents a hydrogen, an alkyl or aralkyl radical;
• R2 represents a hydrogen, an alkyl, aralkyl, or an aryl radical;
• R3 represents a hydrogen, alkyl, including aralkyl, an aryl radical, or forms, with R4, an additional double bond so as to convert the allyl radical into a propargyl radical;
• R4 represents a hydrogen, aryl, alkyl, aralkyl, or, with R3, forms an additional double bond so that the ethylenic bond becomes acetylenic, making it possible to go from an allyl radical to a propargyl radical;
• R5 represents a hydrogen, an aryl, an alkyl, or aralkyl radical;
• R5 and R4 optionally being fractions of said “Ar” group above, such that R5 and R4, and also the carbon which bears them, form a radical Ar;
• optionally, one of R1, R2, R4, R3 and R5 being a specific trivalent, nitrile or acid function, optionally in esterified form;
• R′ is a hydrogen, a protective group, an aryl, an alkyl, or aralkyl, optionally, a chiral alkyl or aralkyl;
• and
• R″ is an allyl or homoallyl radical.