Process for producing optically active dihydropyran derivative

Details Process for producing optically active dihydropyran derivative Process for producing optically active dihydropyran derivative

C - Chemistry, Metallurgy

07

D

260/356.6

C07D 309/28 (2006.01) C07D 493/04 (2006.01) C07F 7/08 (2006.01)

Patent

CA 2038243

ABSTRACT OF THE DISCLOSURE A process for producing an optically active dihydro- pyran derivative represented by formula (1): Image (1) wherein R1, R2, R3, and R4 each represents a hydrogen atom, a lower alkyl group, a tri-lower alkylsilylmethyl group, a lower alkoxycarbonylamino group, or an -OR5 group, wherein R5 represents a lower alkyl group, a lower acyl group, a lower alkoxycarbonyl group, a di-lower alkylcarbamoyl group, or a tri-lower alkylsilyl group, or R1 and R2 are taken together to form a 5- to 7-membered cyclic hydrocarbon group or to form a condensed heterocyclic group with an oxygen atom, or R2 and R3 are taken together to form a 5- to 7-membered cyclic hydrocarbon group or to form a condensed heterocyclic group with an oxygen atom, provided that all of R1, R2, R3, and R4 do not represent hydrogen atoms at the same time; and R6 represents a lower alkyl group, - 23 - which comprises reacting a diene compound represented by formula (2): Image (2) wherein R1, R2, R3, and R4 have the same meanings as defined above, with a glyoxylic acid ester represented by formula (3): Image (3) wherein R6 has the same meaning as defined above, in the presence of a binaphthol-titanium complex represented by formula (4): Image (4) wherein X represents a chlorine atom or a bromine atom, is disclosed. - 24 -

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