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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.
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页码:6846 / 6856
页数:11
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