(S)-TADDOL

(4S,5S)-2,2-Dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanol
CAS Number
93379-48-7
PubChem
Molecular Formula
C31H28O4
Molecular Weight
464.55 g/mol
Chiral Ligands Catalysts
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(S)-TADDOL is a chiral diol ligand developed by Seebach, featuring a rigid C2-symmetric 1,3-dioxolane backbone. It forms powerful chiral Lewis acid catalysts with titanium, boron, and aluminum for diverse enantioselective transformations.

Applications

  • Asymmetric Diels-Alder reactions (Ti-TADDOL)
  • Enantioselective aldol reactions
  • Asymmetric [2+2] cycloadditions
  • Asymmetric alkylation of aldehydes

Specifications

Property Value
CAS 93379-48-7
Molecular Formula C31H28O4
Molecular Weight 464.55 g/mol
Purity >99%
Optical Rotation [α]D +115° (c 1, CHCl3)

Features

  • Rigid C2-symmetric scaffold
  • Forms strong Lewis acid complexes
  • Modular derivatization possible
  • High enantioselectivity for cycloadditions

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