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McCubbin, J.A., Maddess, M.L. and Lautens, M. (2008) Enzymatic Resolution of Chlorohydrins for the Synthesis of Enantiomerically Enriched 2-Vinyloxiranes. Synlett, 2008, 289-293.

has been cited by the following article:

• TITLE: Chemoenzymatic Synthesis of an Enantiomerically Enriched Bicyclic Carbocycle Using Candida parapsilosis ATCC 7330 Mediated Enantioselective Hydrolysis

  AUTHORS: Thangavelu Saravanan, Anju Chadha, Tarur Konikkaledom Dinesh, Namasivayam Palani, Sengottuvelan Balasubramanian

  KEYWORDS: Chemoenzymatic Synthesis, Enantioselective Hydrolysis, Candida parapsilosis ATCC 7330, Hydrolases, Bicyclic Carbocycle

  JOURNAL NAME: International Journal of Organic Chemistry, Vol.5 No.4, December 24, 2015

  ABSTRACT: Enantiomerically enriched (R)-1-(2-bromocycloalkenyl)-3-buten-1-ol and its derivatives were obtained via enantioselective hydrolysis [resolution] with good enantioselectivities (E = 31 to >500) using Candida parapsilosis ATCC 7330. The various reaction parameters were optimized for enantioselective hydrolysis to achieve high enantiomeric excess (ee) and conversions. Among the substrates tested, (RS)-1-(2-bromocyclohex-1-en-1-yl) but-3-yn-1-yl acetate was hydrolysed by the biocatalyst in 12 h to the corresponding (R)-alcohol in 49% conversion and >99 ee. The optically pure allylic alcohol thus obtained was used as a chiral starting material for the synthesis of an enantiomerically enriched bicyclic alcohol effectively establishing achemoenzymatic route.