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

被引:24
作者
Mandai, Hiroki [1 ]
Yasuhara, Hiroshi [1 ]
Fujii, Kazuki [1 ]
Shimomura, Yukihito [1 ]
Mitsudo, Koichi [1 ]
Suga, Seiji [1 ]
机构
[1] Okayama Univ, Grad Sch Nat Sci & Technol, Div Appl Chem, Kita Ku, 3-1-1 Tsushima Naka, Okayama 7008530, Japan
关键词
NONENZYMATIC KINETIC RESOLUTION; ENANTIOSELECTIVE ACYL TRANSFER; MESO-VIC-DIOLS; ASYMMETRIC DESYMMETRIZATION; DMAP DERIVATIVES; MOLECULAR RECOGNITION; CINCHONA ALKALOIDS; ACYLATION; CATALYSTS; 1,2-DIOLS;
D O I
10.1021/acs.joc.7b00992
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We developed an acylative desymmetrization of meso-1,2-diols using a binaphthyl-based N,N-4-dimethylamino-pyridine (DMAP) derivative lh 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 lh play a significant role in achieving high catalytic activity, chemoselectivity of monoacylation, and enantioselectivity.
引用
收藏
页码:6846 / 6856
页数:11
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