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  • 393762 - (4S-trans)-2,2-Dimethyl-α,α,α′,α′-tetra(2-naphthyl)-1,3-dioxolane-4,5-dimethanol

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393762 Aldrich

(4S-trans)-2,2-Dimethyl-α,α,α′,α′-tetra(2-naphthyl)-1,3-dioxolane-4,5-dimethanol

98%

Synonym: (+)-2,3-O-Isopropylidene-1,1,4,4-tetra(2-naphthyl)-D-threitol, (+)-DINOL, (4S,5S)-2,2-Dimethyl-α,α,α′,α′-tetra(2-naphthyl)dioxolane-4,5-dimethanol

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Privileged Ligands and Complexes, TADDOLs More...
InChI Key   QWADMRIAKWGVBF-CXNSMIOJSA-N
assay   98%
optical activity   [α]20/D +116°, c = 1 in ethyl acetate
optical purity   ee: 99% (HPLC)
mp   214-216 °C(lit.)

Description

Packaging

1 g in glass bottle

Application

Reagent for the highly enantioselective addition of primary alkyl Grignards to ketones. Chiral auxiliary used for the asymmetric addition of nucleophiles to carbonyls.

Price and Availability

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3
Protocols & Articles

Articles

Chiral Diols - Aldrich ChemFiles 2007, 7.9, 13.

Apart from numerous examples using TADDOLs in metal-catalyzed asymmetric reactions, Rawal recently reported that TADDOLs could be used as Brønsted acid organocatalysts in highly stereoselective heter...
Aldrich ChemFiles 2007, 7.9, 13.
Keywords: Addition reactions, Aminations, Asymmetric synthesis, Catalysis, Chemfiles, Substitutions

TADDOL

The chiral auxiliaries TADDOLs (α,α,α,α-tetraaryl-1,3-dioxolane-4,5- dimethanols) developed by Seebach's group have found numerous applications in asymmetric synthesis ranging from utilization as sto...
Keywords: Addition reactions, Applications, Asymmetric synthesis, Catalysis, Chiral auxiliaries, Desymmetrizations, Diels-Alder reaction, Fluorinations, Hydrogenations, Metathesis, Nucleophilic additions, Polymerization reactions, Transesterifications

Peer-Reviewed Papers
15

References

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