26923-94-4Relevant academic research and scientific papers
1,3-dioxolan-2-ylium cations from acylfurans: Conversion of furyl ketones to esters under nonoxidative conditions
Bender, John A.,Daves, Samantha,West
, p. 2051 - 2054 (1998)
Acylfurans 3 furnished tosylated glycol monoesters 5 when treated with 1,2-diols in the presence of an equivalent of TsOH. This process likely occurs via protiodefuranation of the intermediate furyl ketals to form 1,3- dioxolan-2-ylium cations 8. Subsequent ring-opening via S(N)2 nucleophilic displacement by p-toluenesulfonate then provides esters 5. When a 1,3-diol was employed, furancontaining ester 9 was formed instead of the standard product through an apparent aldol dimerization/fragmentation pathway.
Deracemization of 1,2-diol monotosylate derivatives by a combination of enzymatic hydrolysis with the Mitsunobu inversion using polymer-bound triphenylphosphine
Shimada, Yasutaka,Usuda, Kazumasa,Okabe, Hirokazu,Suzuki, Tsuguru,Matsumoto, Kazutsugu
experimental part, p. 2802 - 2808 (2010/03/30)
The deracemization of 1,2-diol monotosylate derivatives is achieved by the sequential combination of enzymatic hydrolysis and Mitsunobu inversion using a polymer-bound triphenylphosphine. After the lipase-catalysed hydrolysis of the racemic 2-acetoxyhexyl tosylate, the subsequent Mitsunobu reaction without separation causes an inversion of the resulting (R)-alcohol to give the (S)-enantiomer of the acetate as a single product. In particular, the reaction using the polymer-bound triphenylphosphine also proceeds smoothly, and the product is easily separated by filtration from the polymer-bound reagent and its by-products. This deracemization process is applicable to the preparation of several optically active 1,2-diol monotosylates.
