期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 30, 页码 10315-10319出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201905034
关键词
alcohols; carbamates; chiral Bronsted acids; kinetic resolution; organocatalysis
资金
- NSFC [21702138]
- Shanghai Pujiang Program [17PJ1406300]
- Thousand Talents Plan Youth program
- ShanghaiTech University
A highly enantioselective kinetic resolution of tertiary 2-alkoxycarboxamido allylic alcohols has been achieved through a chiral phosphoric acid catalyzed intramolecular transesterification reaction. Both alkyl,aryl- and dialkyl-substituted tertiary allylic alcohols were resolved with excellent efficiencies, affording both the recovered tertiary alcohols and the carbamate products with high enantioselectivities (with s factors up to 164.6). A gram-scale reaction with 1 mol % catalyst loading and the facile conversion of the enantioenriched products into useful chiral building blocks, such as chiral oxazolidinones and beta-amino alcohols, demonstrate the value of this reaction.
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