E. V. Gorobets, A. V. Kutchin, G. A. Tolstikov, “Stereoselective Synthesis of (1R,4R,6S)-6-(Dibromoaluminio)-7-(methoxymethyl)menth-2-ene and further Preparation of trans-7-(Methoxymethyl)menth-2-ene Hydroxy- and Oxo-derivatives”, Mendeleev Commun., 1993, Volume 3, Issue 5,Pages 217

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Stereoselective Synthesis of (1R,4R,6S)-6-(Dibromoaluminio)-7-(methoxymethyl)menth-2-ene and further Preparation of trans-7-(Methoxymethyl)menth-2-ene Hydroxy- and Oxo-derivatives

E. V. Gorobets^a, A. V. Kutchin^a, G. A. Tolstikov^b

^a Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences, Ufa, Russian Federation
^b N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russian Federation

Abstract: (1R,4R,6R)- and (1R,4R,6S)-7-(Methoxymethyl)menth-2-en-6-ol 7 and 8, (1R,4R)-7-(methoxymethyl)menth-2-en-6-one 10, (1 R,4R)-7-(methoxymethyl)menth-2-ene 5 and their saturated analogues have been synthesized from (1 R,4R,6S)-6-(dibromoaluminio)-7-(methoxymethyl)menth-2-ene 3, prepared under hydroaiumination of the methyl ether of 2-{(1 R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl}ethanol with the LiAIH₄·3AIBr₃ system.

Language: English

DOI: 10.1070/MC1993v003n05ABEH000302