- Novel Base-induced Isomerization of Unsaturated Alcohols to Aldehydes
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A number of allylic and other unsaturated alcohols have been converted into aldehydes by treatment with N-lithioethylenediamine in ethylenediamine (LEDA-EDA) and also with lithium 3-aminopropanamide in 3-aminopropanamine (LAPA-APA).
- Hoffmann, H. M. R.,Koever, Andreas,Pauluth, Detlef
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- Terpenes and Terpenoid Compounds, 17. - Preparation of Oxygenated Tetramethylmethenes and Tetramenthylmenthadienes
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The hydroboration of rac-TM-limonene (1) (TM = tetramethyl) with 9-BBN is chemoselective and allows the functionalization of the isopropenyl side chain to give rac-TM-Δ1-p-Menthen-10-ol (4a,b), the corresponding aldehyde 5a,b, and the acid 6.Protonolysis of the product of hydroboration affords rac-TM-Δ1-p-menthene (7).Hydrochlorination of 1, epoxidation, and treatment with lithium diisopropylamide yields rac-TM-Δ1(7),8-p-menthadien-10-ol (9) which is rearranged by acid into rac-TM-Δ1,8-p-menthadien-10-ol (11).
- Pauluth, Detlef,Hoffmann, H. M. R.
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p. 756 - 764
(2007/10/02)
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