Selective monoacylation of alkane-α,ω-diols using crude acetone powders of animal tissues
|Ryszard Ostaszewski 1, Dominik Koszelewski 1, Marta Komar 1, Adam Redzej 1, Piotr Kiełbasiński 2|
1. Polish Academy of Science, Institute of Organic Chemistry, Kasprzaka 44/52, Warszawa 01-224, Poland
Monofunctionalization of symmetrical substrates bearing two identical substituents continues to be a real challenge for organic chemists, despite a number of attempts that have been described in the literature . Of particular importance is the monoacylation of polymethylene α,ω-diols, since the resulting products are crucial building blocks in the synthesis of various biologically active derivatives, e.g. insect sex pheromones .
In this paper a new methodology of the monoacylation of alkane-α,ω-diols will be presented, which rests upon the use of crude animal tissues (liver or kidney) acetone powders as the source of ester-forming enzymes.
The reaction was performed in various solvents using isopropenyl acetate as the acetylating agent. It should be stressed, that certain crude acetone powders proved superior to a variety of commercially available enzymes. For example, the use of bovine liver acetone powder (BLAP) in the acetylation of octane-1,8-diol in toluene allowed to reach the 87% conversion with a monoacetylation excess of 95%. The influence of the solvents and reaction conditions on the reaction outcome will be discussed and experimental details will be presented.
This work was supported by the network "Synthesis, Structure and Therapeutic Properties of Compounds and Organic Substances".
Presentation: Poster at VI Multidyscyplinarna Konferencja Nauki o Leku, by Adam Redzej
See On-line Journal of VI Multidyscyplinarna Konferencja Nauki o Leku
Submitted: 2008-03-13 13:00 Revised: 2009-06-07 00:48