Chiral Diols

Aldrich ChemFiles 2005, 5.4, 12.

Aldrich ChemFiles 2005, 5.4, 12.

2,5-Hexanediol and 3,6-Octanediol

Enantiomerically pure C2-symmetrical alkanediols such as (2S,5S)-, and (2R,5R)-hexanediol are valuable building blocks for the synthesis of chiral ligands such as (2S,5S)-dimethylpyrrolidine or (2S,5S)-dimethylthiolane (Scheme 24, R = Me). (3R,6R)-Octanediol was used as a convenient starting material for the preparation of enantiomerically pure bis(phospholano)ethane ligands (Scheme 24, R = Et). Their use in Rh-catalyzed highly enantioselective hydrogenation reactions was described by Burk et al.1


Scheme 24


2-Methyl-1,4-butanediol

Huang et al. reported a concise asymmetric total synthesis of (2S,3S,7S)-3,7-dimethylpentadecan-2-yl acetate and propionate, the sex pheromones of the pine sawflies.2 Starting from (S)-2-Methyl-1,4-butanediol, these pheromones are synthesized efficiently as depicted in Scheme 25.


Scheme 25


cis-4-Cyclopentene-1,3-diol 1-acetate

(1R,3S)-(+)-cis-4-Cyclopentene-1,3-diol 1-acetate has proven to be a valuable precursor for the synthesis of carbocyclic nucleosides and prostaglandins (Scheme 26).3


Scheme 26

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Materials

     

References

  1. Burk, M. J. et al. J. Am. Chem. Soc. 1993, 115, 10125.
  2. Huang, P.-Q. et al. J. Org. Chem. 2004, 69, 3964.
  3. (a) Theil, F. et al. J. Chem. Soc., Perkin Trans. I 1996, 255; (b) Myers, A. G. et al. Tetrahedron Lett. 1996, 37, 3083; (c) Paquette, L. A. et al. Org. Synth. 1995, 73, 36.

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