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US 9,284,246 B2Granted
Method for producing optically active 2,3-dihydrofarnesal
AssigneeTakasago International Corporation
InventorsHideo Ujihara, Mitsuhiko Fujiwhara
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Abstract
A method for producing an optically active 2,3-dihydrofarnesal of formula (1) is disclosed. The method includes subjecting β-farnesene f formula (2) to amination in the presence of a lithium salt of an amine to obtain (2E)-farnesyl allylamine of general formula (3); subjecting the (2E)-farnesyl allylamine to asymmetric isomerization to obtain an optically active farnesyl enamine of general formula (4); and subjecting the optically active farnesyl enamine to solvolysis:
Claims2
A method for producing an optically active 2,3-dihydrofarnesal of formula (1):
- wherein * represents an asymmetric carbon atom, the method comprising:
- subjecting β-farnesene of formula (2) to amination in the presence of a lithium salt of an amine:
- to obtain (2E)-farnesyl allylamine of general formula (3):
- wherein R1 and R2 are each independently selected from the group consisting of a hydrogen atom, optionally substituted alkyl groups having 1 to 20 carbon atoms, optionally substituted 3-to 8-membered alicyclic groups, optionally substituted aryl groups having 6 to 15 carbon atoms, optionally substituted heterocyclic groups having 2 to 15 carbon atoms, and optionally substituted aralkyl groups having 7 to 12 carbon atoms, provided that R1 and R2 do not represent hydrogen atoms at the same time, or R1 and R2 may be bonded to each other to form a ring;
- subsequently subjecting the (2E)-farnesyl allylamine to asymmetric isomerization to obtain an optically active farnesyl enamine of general formula (4):
- wherein R1, R2, and * have the same meanings as defined above;
- and
- further subjecting the optically active farnesyl enamine to solvolysis.
5 more elements
Dependencies are inferred from the claim text.