4-hydroxyalkanoic acid 2-alken

This section covers the hydroboration-oxidation of alkenes to give alcohols. The author chooses to include this under oxidation since an oxygen atom is introduced into the molecule. This reaction can be performed in a stereocontrolled fashion and it is these methods that are highlighted here. In addition, one similar reductive-oxidation reaction is included, since it is an extremely facile route to benzyl alcohols and a-hydroxyalkanoic acids. 

A range of aromatic alkenes and acrylic acid derivatives have been converted into benzyl alcohols and a-hydroxyalkanoic acids in good yields by a reductive oxidation process. This reaction is accomplished by reaction with oxygen and triethylsilane with a cobalt(II) catalyst, followed by treatment with trialkyl phosphites (equation 30)154. The aromatic olefins may also be converted into the corresponding acetophenone in a modified procedure where the trialkyl phosphite is removed155. In a similar reaction 2,4-alkadienoic acids are converted into 4-oxo-2-alkenoic acids156. 

A petroleum-degrading strain HD-1 was able to grow autotrophically by using CQ2 as sole carbon source. Inside the cell there accumulated alkane/alkene besides fatty acids or poly-p-hydroxyalkanoic acid. Fatty acids and fatty aldehydes were shown to be reduced to alkane/alkene by anaerobic incubation with the HD-1 cell lysate. 

Marhere, P. (2009) Production of Alkenes by Enzymatic Decarboxylation of 3-Hydroxyalkanoic acids,... 

Part 2 Conversion into acettme-butanol. Bioresour Technol 42(3) 205-217 Marchionna M, Di Girolamo M, Patrini R (2001) Light olefins dimerization to high quality gasoline ctnnponents. Catal Today 65(2-4) 397-403 Marliere P (2010) Production of alkenes by enzymatic decarboxylation of 3-hydroxyalkanoic acids. Google Patents... 

Marliere P et al (2013) Production of alkenes by combined enzymatic conversion of 3-hydroxyalkanoic acids. Google Patents... 

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