Process for producing optically active dihydropyran derivative

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

1991-03-13

1992-10-13

Chan, Nicky

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549424, 549420, 549419, 549417, 549405, 549404, 549399, 549396, 549355, 549214, C07D30906

Patent

active

051552400

ABSTRACT:
A process for producing an optically active dihydropyran derivative represented by formula (1): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 each represents a hydrogen atom, a lower alkyl group, a tri-lower alkylsilylmethyl group, a lower alkoxycarbonylamino group, or an --OR.sup.5 group, wherein R.sup.5 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 R.sup.1 and R.sup.2 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 R.sup.2 and R.sup.3 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 R.sup.1, R.sup.2, R.sup.3, and R.sup.4 do not represent hydrogen atoms at the same time; and R.sup.6 represents a lower alkyl group, which comprises reacting a diene compound represented by formula (2): ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 have the same meanings as defined above, with a glyoxylic acid ester represented by formula (3): ##STR3## wherein R.sup.6 has the same meaning as defined above, in the presence of a binaphthol-titanium complex represented by formula (4): ##STR4## wherein X represents a chlorine atom or a bromine atom, is disclosed.

REFERENCES:
Terada et al., Lecture Preprint II, 59th Spring Annual Meeting of Chemical Society of Japan, p. 1356 (Mar. 14, 1990).
Tetrahedron, vol. 32, pp. 2957-2959 (1976).
J. Org. Chem., pp. 1440-1456 (1985).
Tetrahedron, vol. 42, pp. 2787-2801 (1986).
J. Chem. Soc., Chem. Commun., pp. 676-677 (1987).
Synthesis, pp. 544-545 (1987).
J. Chem. Soc., Chem. Commun., pp. 540-542 (1983).

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