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  • Title: Minor enantiomer recycling: metal catalyst, organocatalyst and biocatalyst working in concert.
    Author: Wingstrand E, Laurell A, Fransson L, Hult K, Moberg C.
    Journal: Chemistry; 2009 Nov 09; 15(44):12107-13. PubMed ID: 19768712.
    Abstract:
    A minor enantiomer recycling one-pot procedure employing two reinforcing chiral catalysts has been developed. Continuous regeneration of the achiral starting material is effected via selective enzyme-catalyzed hydrolysis of the minor product enantiomer from Lewis acid-Lewis base catalyzed addition of acyl cyanides to prochiral aldehydes in a two-phase solvent system. The process provides O-acylated cyanohydrins in close to perfect enantioselectivities, higher than those obtained in the direct process, and in high yields. A combination of a (S,S)-salen Ti Lewis acid and Candida antarctica lipase B provides the products with R absolute configuration, whereas the opposite enantiomer is obtained from the (R,R)-salen Ti complex and Candida rugosa lipase.
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