Process of preparing optically active allyl compound
AssigneesNational University Corporation Chiba University, Nippon Chemical Industrial Co., Ltd.
InventorsTsuneo Imamoto, Kazuhiro Yoshida, Miwako Nishimura, Aya Koide
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Abstract
Disclosed is a process of preparing an optically active allyl compound, e.g., as represented by formula (III): comprising asymmetrically coupling an allyl compound with an organic nucleophilic compound in the presence of a catalyst. The catalyst is preferably a transition metal complex compound having a phosphine ligand. The phosphine ligand is preferably a 2,3-bis(dialkylphosphino)pyrazine derivative. The pyrazine derivative is preferably a quinoxaline derivative. The transition metal is preferably palladium.
Claims1
A process of preparing an optically active allyl compound represented by formula (III):
- wherein R1, R3, and R4 each represent a hydrogen atom;
- R2 and R5 each represent a phenyl group;
- Nu represents a nucleophilic group selected from an α-ketocarbanion group, an amino group, and a substituted amino group;
- and the asterisk * indicates an asymmetric center,
- or an optically active allyl compound represented by formula (IV):
- wherein R1, R2, R3, R4, R5, Nu, and * are as defined above,
- or a mixture of the compound of formula (III) and the compound of formula (IV),
- the process comprising asymmetrically coupling an allyl compound represented by formula (I):
- wherein R1, R2, R3, R4, and R5 are as defined above;
- and E represents a leaving group which is a carboxylic ester group, with an organic nucleophilic compound represented by formula (II):
- Nu-H (II)
- wherein Nu is as defined above, in the presence of a Pd complex compound catalyst having a quinoxaline derivative represented by formula (a) as a ligand:
- wherein * is as defined above.
Dependencies are inferred from the claim text.