2017年8月
Hydrogen Bonding-Assisted Enhancement of the Reaction Rate and Selectivity in the Kinetic Resolution of d,l-1,2-Diols with Chiral Nucleophilic Catalysts
ADVANCED SYNTHESIS & CATALYSIS
- ,
- ,
- ,
- 巻
- 359
- 号
- 16
- 開始ページ
- 2778
- 終了ページ
- 2788
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1002/adsc.201700057
- 出版者・発行元
- WILEY-V C H VERLAG GMBH
An extremely efficient acylative kinetic resolution of d,l-1,2-diols in the presence of only 0.5 mol% of binaphthyl-based chiral N,N-4-dimethylaminopyridine was developed (selectivity factor of up to 180). Several key experiments revealed that hydrogen bonding between the tert-alcohol unit(s) of the catalyst and the 1,2-diol unit of the substrate is critical for accelerating the rate of monoacylation and achieving high enantioselectivity. This catalytic system can be applied to a wide range of substrates involving racemic acyclic and cyclic 1,2-diols with high selectivity factors. The kinetic resolution of d,l-hydrobenzoin and trans-1,2-cyclohexanediol on a multigram scale (10 g) also proceeded with high selectivity and under moderate reaction conditions: (i) very low catalyst loading (0.1 mol%); (ii) an easily achievable low reaction temperature (0 degrees C); (iii) high substrate concentration (1.0M); and (iv) short reaction time (30 min).
- リンク情報
- ID情報
-
- DOI : 10.1002/adsc.201700057
- ISSN : 1615-4150
- eISSN : 1615-4169
- Web of Science ID : WOS:000407782300011