期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2020, 期 6, 页码 654-661出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201901583
关键词
Lipase; Axial Chirality; Enantiodivergent Synthesis; Desymmetrization
资金
- JSPS KAKENHI [18HO4411, 18H02556]
- Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from AMED [JP19am0101084]
- Grants-in-Aid for Scientific Research [18H02556] Funding Source: KAKEN
The enzymatic acylative desymmetrization of sigma-symmetric 2'-halo-1,1'-biphenyl-2,6-diols was achieved for the first time using commercially available Burkholderia cepacia lipase immobilized on diatomaceous earth to give (S)-mono esters. The hydrolytic desymmetrization of the corresponding diacetates was also achieved using the same lipase to give (R)-mono esters. Our results, therefore, demonstrate that a single lipase can conduct the enantiodivergent synthesis of axially chiral biphenyl compounds in high chemical and optical yields.
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