4.6 Article

Dinuclear zinc-catalyzed asymmetric desymmetrization of acyclic 2-substituted-1,3-propanediols: A powerful entry into chiral building blocks

期刊

CHEMISTRY-A EUROPEAN JOURNAL
卷 14, 期 25, 页码 7648-7657

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200800623

关键词

asyrnmetric catalysis; chiral building blocks; desymmetrization; enantioselectivity; propanediol

资金

  1. National Science Foundation
  2. National Institutes of Health [GM-33049]
  3. Eli Lilly Company
  4. NIH division or Research Resources
  5. NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM033049] Funding Source: NIH RePORTER

向作者/读者索取更多资源

The asymmetric acylation of meso-2-substituted-1,3-propanediols by using an amphoteric chiral dinuclear zinc catalyst is described. It is has been demonstrated that both 2-alkyl- and 2-aryl-1,3-propanediols can be desymmetrized in high yields and enantioselectivities by using the same family of ligands. Given that both antipodes of the chiral catalyst are available, both enantiomers of the desymmetrized product can be obtained from the same starting material. The synthetic utility of the desymmetrized products has been demonstrated by the synthesis of several chiral building blocks with high enantiomeric purities.

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