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Synthesis 2001; 2001(3): 0423-0426
DOI: 10.1055/s-2001-11444
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Chemoenzymatic Synthesis of (2R)-2-Hydroxyundecan-6-one

Edina Ljubović* , Vitomir Šunjić
  • *Rudđer Bošković Institute, P.O.B. 80, 10002 Zagreb, Croatia; Fax + 3 85(1)4 68 01 95; E-mail: sunjic@rudjer.irb.hr
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Publication Date:
31 December 2001 (online)

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Optimisation of kinetic resolution of racemic 5-hydroxyhexanenitrile (2) was performed; acetylation with vinyl acetate, catalyzed by Pseudomonas cepacia lipase immobilized on ceramics (PS-C) in n-hexane, afforded (5R)-acetoxy-hexanenitrile [(R)-3] with 94% ee and 94% yield; E = 83. Deacetylation of (R)-3, protection of (R)-2 by tert-butyldimethylsilyl group, grignard reaction of (R)-4 with n-pentyl magnesium bromide, and final deprotection of (R)-5 afforded the title compound (R)-6 in 32% overall yield from 1 and 94% enantiomeric purity. Absolute configuration of (R)-6 was assigned by chemical correlations to (5R)-methyl-5-pentanolide [(R)-7].

enzymes - kinetic resolution - Grignard reaction - tert-butyldimethylsilyl (TBDMS)