Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 13, Pages 6846-6856Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00992
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Funding
- JSPS [17K17903]
- MEXT (Japan)
- Grants-in-Aid for Scientific Research [16H01155, 16K05777, 16K05695, 17K17903, 17J02283] Funding Source: KAKEN
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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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