Alpha alkylation of aldehyde with a polycyclic olefin
AssigneeFirmenich SA
InventorsJulie Quintaine, David W. C. MacMillan
Life of this patent
Estimating the term…
Abstract
The alpha alkylation of an aldehyde with a polycyclic olefin followed by a ring opening step is presented in order to provide a compound of formula (I) in the form of any one of its stereoisomers or a mixture thereof and where in R represents a hydrogen atom or C1-8 linear alkyl group; R1, R2, R3, and R4 represent, when taken separately, independently of each other, a hydrogen atom or a C1-2 linear alkyl group or a C3-4 linear or branched alkyl group; or R2 and R3, when taken together, represent a C4-10 linear, branched or cyclic alkanediyl group and n is 1 or 2 is presented.
Claims16
A process for the preparation of a compound of formula
- in a form of any one of its stereoisomers or a mixture thereof and wherein R represents a hydrogen atom or C1-8 linear alkyl group;
- R1, R2, R3 and R4 represent, when taken separately, independently of each other, a hydrogen atom or a C1-2 linear alkyl group or a C3-4 linear or branched alkyl group;
- or R2 and R3, when taken together, represent a C4-10 linear, branched or cyclic alkanediyl group and n is 1 or 2;
- comprising the step of an alpha alkylation of an aldehyde of formula R—CH2—CHO, wherein R has the same meaning as above, with an olefin compound being a fused or bridged bicyclic or tricyclic compound with a methylene group in alpha of a ring junction;
- said step being performed in the presence of a photoredox catalyst, a hydrogen atom transfer donor, a secondary amine and light.
A composition of matter comprising:
- a) a compound of formula
- in a form of any one of its stereoisomers or a mixture thereof and wherein R represents a hydrogen atom or C1-8 linear alkyl group;
- R1, R2, R3 and R4 represent, when taken separately, independently of each other, a hydrogen atom or a C1-2 linear alkyl group or a C3-4 linear or branched alkyl group or R2 and R3, when taken together, represent a C4-10 linear, branched or cyclic alkanediyl group and n is 1 or 2;
- and
- b) a compound of formula
- in a form of any one of its stereoisomers or a mixture thereof;
- and wherein R represents a hydrogen atom or a C1-8 linear alkyl group;
- R1 represents a hydrogen atom or a C1-2 linear alkyl group or a C3-4 linear or branched alkyl group;
- and R5, R6 and R7 are taken together and represent a C4-12 linear, branched or alicyclic alkanetryil.
Dependencies are inferred from the claim text.