Novel process for preparing semi-caronic aldehydes

Details Novel process for preparing semi-caronic aldehydes Novel process for preparing semi-caronic aldehydes

1988-12-09

1991-04-02

Lone, Werren B.

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

Organic compounds

Oxygen containing

560124, 568485, C07C 4558

Patent

active

050048406

ABSTRACT:
A novel process for the preparation of compounds of the formula ##STR1## with cis or trans structure in racemic or optically active form wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and aryl of 6 to 12 carbon atoms comprising reacting an optically active isomer, or racemate of the formula ##STR2## wherein R has the above definition and the way line indicates Z or E geometry with a gem-dimethyl cyclopropanation agent if there is Z geometry to obtain a compound of the formula ##STR3## or if the geometry is E with a gem-dimethyl cyclopropanation agent other than isopropylidene triphenyl phosphorane to obtain a compound of the formula ##STR4## wherein R has the above definition and the cyclopropane ring has the trans configuration and either hydrolyzing the compound of formula III or IIIa to obtain a compound of the formula ##STR5## and then cleaving the 4,5 bond to obtain the corresponding compound of formula I or simultaneously cleaving the 4,5 bond and hydrolyzing the dioxolane group to obtain the corresponding compound of formula I and novel intermediates.

REFERENCES:
patent: 4551545 (1985-11-01), Frank-Neumann et al.
Mulzer et al., "Chemical Abstracts", vol. 98 (1983), 160,949t.
Mulzer et al., "Chemical Abstracts", vol. 101 (1984) 23776a.

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