Optically active 2,2-dimethyl-1,3-dioxin-4-ones and method for p

Details Optically active 2,2-dimethyl-1,3-dioxin-4-ones and method for p Optically active 2,2-dimethyl-1,3-dioxin-4-ones and method for p

1992-12-15

1994-03-08

Cintins, Marianne M.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549292, 549294, 549518, 549561, C07D30127, C07D30910, C07D30930

Patent

active

052928918

ABSTRACT:
There are provided novel and optically active 2,2-dimethyl-1,3-dioxin-4-ones which are useful as starting materials for physiologically active compounds, functional materials or the like. Provided are optically active 5,6-epoxyhexanoic acid esters and novel optically active 6-substituted tetrahydropyran-2-one derivatives. That is, optically active 6-chloromethyltetrahydropyran-2-one can be synthesized by lactonizing optically active 2,2-dimethyl-6-(3-chloro-2-hydroxypropyl)-1,3-dioxin-4-one to form optically active 6-chloromethyltetrahydropyran-2,4-dione; reacting the thus formed compound with hydrogen in the presence of a catalyst to obtain optically active 6-chloromethyl-4-hydroxytetrahydropyran-2-one; subjecting this compound to a dehydration reaction, thereby obtaining optically active 6-chloromethyldihydropyran-2-one; reacting this compound with hydrogen in the presence of a catalyst to form optically active 6-chloromethyltetrahydropyran-2-one; and then treating this compound under basic conditions to prepare an optically active 5,6-epoxyhexanoic acid ester represented by the formula (6) ##STR1## (wherein the symbol * represents an asymmetric carbon atom, and R is a methyl group or an ethyl group).

REFERENCES:
Sakaki et al., Chemistry Letters, No. 6, Jun. 1990, pp. 901-904.
Chisso Corp., Patent Abstracts of Japan, vol. 14, No. 439 (C-761) 19 Sep. 1990 JP-A-2 171 192 2 Jul. 1990.
Sakaki et al., Tetrahedron, vol. 47, No. 32, pp. 6197-6214 (1991).
Sato et al., Chemical Abstracts, vol. 116 (1992) Abstract No. 41376j.
Sakaki et al., J. Chem. Soc., Chem. Commun. (1991) pp. 434-435.
Sakaki et al., Tetrahedron: Asymmetry, vol. 2, No. 5 pp. 343-346 (1991).

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