Kinetic resolutions succinic anhydride

Figure 57 Some of the biocatalytic steps using lipase developed at BASF Lipase-catalyzed kinetic resolution of a) phenyl ethanol 18 using succinic anhydride, b) Secondary amine 120 using ethyl methoxyacetate as acyl...

In 2001, Deng and coworkers found that nucleophilic catalysts such as (DHQD)2AQN (11) can also affect the parallel kinetic resolution of racemic anhydrides by alcoholysis, that is, the two substrate enantiomers are converted into regioisomeric esters. A variety of monosubstituted racemic succinic anhydrides were converted in the presence of (DHQD)2AQN (11, 15-20 mol%) and allyl alcohol as a nucleophile to both regioisomeric hemiesters 49 and 50 with synthetically reliable ee values (up to 98% ee) and yields (Scheme 11.26) [41]. The obtained regioisomeric 2-or 3- aryl succinates could be converted to the P- and a-aryl-y-butylolactones, which constitute valuable synthons for various pharmaceuticals. 

KINETIC RESOLUTION OF A SECONDARY ALCOHOL (1-INDANOL) BY LIPASE-CATALYZED SUCCINYLATION WITH SUCCINIC ANHYDRIDE... 

Kinetic resolution 1 -indanol by acylation with succinic anhydride yields products that are easily separated by liquid-liquid extraction. 

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