(+)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane Guide

(+)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane is a C2-symmetric chiral diol derived from the tartrate framework, widely employed as a chiral ligand and auxiliary in asymmetric synthesis and stereoselective catalysis.

Chemical Name

(+)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane

SKU

B120911

Core Structural Feature

C2-symmetric 1,3-dioxolane ring bearing two diphenylcarbinol groups derived from L-(+)-tartaric acid

Primary Application

Chiral ligand and auxiliary in asymmetric addition, Diels-Alder, and titanium-mediated reactions

Symmetry Class

C2-symmetric diol (TADDOL-type)

Stereochemical Origin

Derived from naturally available (+)-tartaric acid, ensuring defined absolute configuration

Chemical Structure and Properties

(+)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane belongs to the TADDOL (tetraaryl-1,3-dioxolane-4,5-dimethanol) family of chiral diols. Its molecular framework consists of a five-membered 1,3-dioxolane ring protected as the acetonide (isopropylidene ketal) at the 2-position, with each of the 4- and 5-ring carbons bearing a diphenylcarbinol substituent. This arrangement confers strict C2 rotational symmetry upon the molecule.

The two hydroxyl groups project on the same face of the dioxolane ring and are capable of forming well-defined chiral pockets through intramolecular and intermolecular hydrogen bonding. The phenyl rings adopt a propeller-like orientation that creates a pronounced chiral environment suitable for enantioselective recognition. The positive optical rotation (+) indicates derivation from L-(+)-tartaric acid, fixing the (4R,5R) absolute configuration.

As a solid at ambient temperature, the compound exhibits good stability under standard laboratory storage conditions. Its solubility in common organic solvents such as dichloromethane, THF, and toluene facilitates its use across a broad range of synthetic protocols.

Role in Asymmetric Synthesis

The compound functions principally as a chiral ligand for transition metals, most notably titanium(IV). When combined with titanium alkoxides such as Ti(OiPr)4, it forms well-defined chiral titanium complexes that serve as Lewis acid catalysts for enantioselective transformations. The resulting titanium-TADDOL complexes have been documented to catalyze asymmetric Diels-Alder cycloadditions, hetero-Diels-Alder reactions, and carbonyl-ene reactions with useful levels of enantioselectivity.

Beyond titanium chemistry, the diol can coordinate to other oxophilic metal centers including zinc, boron, and aluminum, broadening its utility in asymmetric addition reactions. In nucleophilic addition to aldehydes—particularly the Reformatsky-type and organozinc additions—chiral dioxolane diols of this class have been shown to exert significant facial selectivity.

The compound also serves as a chiral controller in stoichiometric auxiliary strategies. Its rigid tartrate-derived scaffold transmits stereochemical information efficiently to prochiral reaction centers, making it a versatile reagent for constructing enantiomerically enriched building blocks used in pharmaceutical and natural product synthesis.

Handling, Storage, and Safety

The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated area away from incompatible materials such as strong oxidizers and strong acids. Standard laboratory personal protective equipment—including nitrile gloves, safety glasses, and a laboratory coat—should be worn when handling the reagent.

As with most fine organic reagents, prolonged or repeated exposure should be minimized. In the event of skin contact, the affected area should be washed thoroughly with soap and water. If eye contact occurs, immediately flush with copious amounts of water and seek medical attention.

For long-term preservation of optical purity and reagent integrity, storage under an inert atmosphere (nitrogen or argon) at reduced temperature (2–8 °C) is recommended. Users should consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for complete hazard information before use.

Procurement and Quality Specifications

Aladdin Scientific supplies (+)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane under SKU B120911. Researchers requiring this reagent for asymmetric synthesis programs should verify purity and optical rotation data on the accompanying Certificate of Analysis (CoA) prior to use, as these parameters are critical for reproducible enantioselectivity outcomes.

When evaluating reagent specifications, key quality indicators include chemical purity (typically assessed by HPLC or GC), optical purity (enantiomeric excess, measured by polarimetry or chiral HPLC), and moisture content. Procurement teams should request lot-specific CoA documentation to ensure batch-to-batch consistency, particularly for GMP-adjacent research activities.

For bulk quantities or custom packaging requirements, laboratory managers and procurement officers are encouraged to contact Aladdin Scientific's customer service team directly. Volume pricing and lead-time information can be obtained through the official Aladdin Scientific online platform or sales representatives.

Frequently asked questions

What is the primary use of (+)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane in research?

Its primary use is as a C2-symmetric chiral diol ligand in asymmetric synthesis. It forms chiral metal complexes, particularly with titanium(IV), that catalyze enantioselective reactions including Diels-Alder cycloadditions, carbonyl-ene reactions, and nucleophilic additions to aldehydes.

How should this chiral dioxolane reagent be stored to maintain its optical purity?

The reagent should be stored in a tightly sealed container under an inert atmosphere (nitrogen or argon) at 2–8 °C, in a cool and dry location away from moisture, strong oxidizers, and strong acids. Proper storage conditions prevent racemization and hydrolytic degradation that could compromise enantioselectivity in downstream applications.

How does the TADDOL-type structure of this compound contribute to its effectiveness as a chiral ligand?

The TADDOL-type structure provides a rigid, C2-symmetric scaffold in which two hydroxyl groups converge to form a well-defined chiral coordination pocket. The four phenyl groups create a sterically demanding chiral environment through their propeller-like arrangement, allowing the ligand to effectively discriminate between the two enantiotopic faces of a prochiral substrate when bound to a Lewis acidic metal center.

What quality parameters should I verify before using SKU B120911 in an asymmetric synthesis?

Before use, verify the chemical purity (by HPLC or GC), optical rotation value (compared against the specification for the (+)-enantiomer), and enantiomeric excess (ee) as stated on the lot-specific Certificate of Analysis. Moisture content is also relevant, as water can interfere with metal coordination and reduce catalytic performance.

References

1. Seebach, D.; Beck, A. K.; Heckel, A. TADDOLs, Their Derivatives, and TADDOL-Analogues: Versatile Chiral Auxiliaries. Angewandte Chemie International Edition, 2001, 40, 92–138. doi:10.1002/1521-3773(20010105)40:1<92::AID-ANIE92>3.0.CO;2-K
2. Narasimhan, S.; Swarnalakshmi, S.; Balakumar, R. TADDOL and its metal complexes in asymmetric synthesis. Synthetic Communications, 2004.

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