- Desymmetrization of meso-1,2-Diols by a Chiral N,N-4-Dimethylaminopyridine Derivative Containing a 1,1′-Binaphthyl Unit: Importance of the Hydroxy Groups
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We developed an acylative desymmetrization of meso-1,2-diols using a binaphthyl-based N,N-4-dimethylaminopyridine (DMAP) derivative 1h with tert-alcohol substituents. The reaction proceeds with a wide range of acyclic meso-1,2-diols and six-membered-ring meso-1,2-diols to provide a monoacylate selectively with a high enantiomeric ratio (er). Only 0.1 mol % of the catalyst facilitated the reaction within a short reaction time (3 h) to afford enantio-enriched monoacylated products in moderate to good yield. Several control experiments revealed that the tert-alcohol units of catalyst 1h play a significant role in achieving high catalytic activity, chemoselectivity of monoacylation, and enantioselectivity.
- Mandai, Hiroki,Yasuhara, Hiroshi,Fujii, Kazuki,Shimomura, Yukihito,Mitsudo, Koichi,Suga, Seiji
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p. 6846 - 6856
(2017/07/17)
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- Asymmetric desymmetrization of meso-diols by C2-symmetric chiral 4-pyrrolidinopyridines
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In this work we developed C2-symmetric chiral nucleophilic catalysts which possess a pyrrolidinopyridine framework as a catalytic site. Some of these organocatalysts effectively promoted asymmetric desymmetrization of meso-diols via enantioselective acylation.
- Schedel, Hartmut,Kan, Keizo,Ueda, Yoshihiro,Mishiro, Kenji,Yoshida, Keisuke,Furuta, Takumi,Kawabata, Takeo
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supporting information
p. 1778 - 1787,10
(2020/09/16)
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