Chemoenzymatic Synthesis of an Enantiomerically Enriched Bicyclic Carbocycle Using <i>Candida parapsilosis</i>ATCC 7330 Mediated Enantioselective Hydrolysis

• 作者: Anju Chadha Namasivayam Palani Sengottuvelan Balasubramanian Tarur Konikkaledom Dinesh Thangavelu Saravanan
• 来源期刊: 有机化学国际期刊(英文)
• 学科: 化学
• 关键词: CHEMOENZYMATIC Synthesis Enantioselective Hydrolysis Candida parapsilosis ATCC 7330 HYDROLASES BICYCLIC Carbocycle
• 年，卷（期）: 2015,（4）
• 页码范围: 271-281
• 页数: 11页
• 分类号: O6

摘要

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.