Stereoselective synthesis of the dimethyl acetals of. beta. ,. gamma. -unsaturated aldehydes from alkyl trans-2-methoxypropyl ketones

Journal Article · Thu Jan 09 23:00:00 EST 1986 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:6286377

Kulinkovich, O G; Tishchenko, I G; Sorokin, V L

trans-(2-Methoxycyclopropyl)carbinols were obtained in the form of equimolar mixtures of diastereomers by the reaction of the respective alkyl trans-2-methoxy-cyclopropyl ketones with lithium aluminum hydride or organometallic compounds. Methanolysis of the products in an acidic medium leads to high yields of the dimethyl acetals of trans- and cis-..beta..,..gamma..-unsaturated aldehydes, in which the content of the trans isomer amounts to 55-70%. The dimethyl acetals of trans-..beta..-..gamma..-unsaturated aldehydes can be produced by this method with greater stereoselectivity by reduction in the degree of transformation of the initial carbinols.

• Research Organization: V.I. Lenin Belorussian State Univ., Minsk, USSR
• OSTI ID: 6286377
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 21:8; ISSN JOCYA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ACETALS
ALCOHOLS
ALDEHYDES
ALKALI METAL COMPOUNDS
ALUMINIUM COMPOUNDS
ALUMINIUM HYDRIDES
CARBON TETRACHLORIDE
CATALYTIC EFFECTS
CHEMICAL REACTION YIELD
CHEMICAL SHIFT
CHLORINATED ALIPHATIC HYDROCARBONS
CHLOROFORM
CHROMATOGRAPHY
COUPLING
DEUTERIUM COMPOUNDS
ETHERS
HALOGENATED ALIPHATIC HYDROCARBONS
HYDRIDES
HYDROGEN COMPOUNDS
HYDROXY COMPOUNDS
INTERMEDIATE COUPLING
ISOMERS
J-J COUPLING
KETONES
LITHIUM COMPOUNDS
LITHIUM HYDRIDES
METHANOL
NMR SPECTRA
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANOMETALLIC COMPOUNDS
SEPARATION PROCESSES
SPECTRA
STEREOCHEMISTRY
SYNTHESIS
YIELDS