4.6 Article

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

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 14, Issue 25, Pages 7648-7657

Publisher

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

Keywords

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

Funding

  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

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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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